Asymmetric synthesis: the essentials
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Weinheim
WILEY-VCH
2008
|
| Ausgabe: | 2., completely rev. ed. |
| Schlagworte: | |
| Online-Zugang: | http://deposit.dnb.de/cgi-bin/dokserv?id=2774561&prov=M&dok_var=1&dok_ext=htm Inhaltsverzeichnis Klappentext |
| Beschreibung: | Literaturangaben |
| Beschreibung: | XL, 355 S. Ill., graph. Darst. |
| ISBN: | 9783527320936 |
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| 245 | 1 | 0 | |a Asymmetric synthesis |b the essentials |c ed. by Mathias Christmann and Stefan Bräse |
| 250 | |a 2., completely rev. ed. | ||
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2008 | |
| 300 | |a XL, 355 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Literaturangaben | ||
| 650 | 7 | |a Chiraliteit |2 gtt | |
| 650 | 7 | |a Enantiomeren |2 gtt | |
| 650 | 7 | |a Stereochemie |2 gtt | |
| 650 | 7 | |a Stereoselectiviteit |2 gtt | |
| 650 | 7 | |a Synthese (chemie) |2 gtt | |
| 650 | 4 | |a Asymmetric synthesis | |
| 650 | 0 | 7 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
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| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Christmann, Mathias |d 1972- |e Sonstige |0 (DE-588)122971035 |4 oth | |
| 700 | 1 | |a Bräse, Stefan |e Sonstige |4 oth | |
| 856 | 4 | |u http://deposit.dnb.de/cgi-bin/dokserv?id=2774561&prov=M&dok_var=1&dok_ext=htm | |
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Datensatz im Suchindex
| _version_ | 1804137243215921152 |
|---|---|
| adam_text | IX
Contents
Foreword V
Message from the Editors
XXV
List of Abbreviations
XXVII
Named and Unnamed Reactions
XXXI
List of Contributors
XXXIII
Part I Chiral Auxiliaries in Asymmetric Synthesis
Introductory Chapter
3
David A. Evans,
Günter Helmchen
and Magnus Raping
Background
3
Results
4
Summary
7
CV
of David A. Evans
8
CV
of
Günter Helmchen
S
CV
of Magnus
Rüping 9
Selected Publications
9
Asymmetric Epoxidation of Pentadienols
10
Reinhard
Bruckner
Background
10
Objective: Making Building Blocks for the
Synthesis of
1,3,5,7,—
-Polyols from Epoxyalcohols
11
Results
12
Asymmetric Epoxidation of a Conjugated Pentadienol
12
Asymmetric Epoxidation of a Nonconjugated Pentadienol
13
CV
of
Reinhard
Bruckner IS
Selected Publications
16
X
Contents
Asymmetrie
Synthesis using Sulfur-Nitrogen Reagents
17
Franklin A. Davis
Background
17
Results
17
Asymmetric Oxidations using N-Sulfonyloxaziridines
17
Asymmetric Fluorination of Enolates with N-Fluoro^lO-Camphorsultams
19
Asymmetric Synthesis of
Amine
Derivatives using
Enantiopure Sulfinimines (N-Sulfinyl Imines)
19
Outlook
20
CV
of Franklin A. Davis
20
Selected Publications
22
Asymmetric Syntheses with
SAMP^RAMP-Hydrazones
23
Dieter
Enders
and Wolfgang Bettray
Background
23
Strategy
24
Results
25
Application for the Synthesis of Natural Products
26
Other Asymmetric Syntheses from the
Enders
Group
27
Conclusions and Future Perspectives
27
CV
of Dieter
Enders 27
Selected Publications
28
Asymmetric Allylation Reactions
29
Reinhard W.
Hoffmann
Background
29
Results
29
Type (I) Allylmetallation of Aldehydes
29
Second Generation Allylmetallation Reagents
31
CV
of
Reinhard W.
Hoffmann
32
Selected Publications
33
Carbohydrates as Chirai Auxiliaries
34
Horst Kunz
Introduction
34
Results
34
Carbohydrate Auxiliaries in
Cycloaddition
Reactions
34
Conjugate Addition Reactions Directed by Carbohydrate Auxiliaries
35
Glycosylamines in Stereoselective Synthesis
36
Conclusions
38
CV
of
Horst Kunz 38
Selected Publications
38
Contents
XI
The Use of Chiral Oxazolines in early
C
-С
Bond Forming Reactions
39
Albert I. Meyers
Background
39
Results
40
CV
of Albert I. Meyers
41
Selected Publications
41
Asymmetric Synthesis of Amines and
Amino
Acids from Amines
42
Shun-Ichi Murahashi and Yasushi
Imada
Background
42
Strategy
43
Results
43
Diastereoselective Reactions of Nitrones
43
Enantioselective Reactions of Nitrones
44
Conclusions and Future Perspectives
46
CV
of Shun-Ichi Murahashi
46
Selected Publications
47
Part II Metal-catalyzed Asymmetric Synthesis
Introductory Chapter
51
Masakatsu Shibasaki and Shigeki Matsunaga
Introduction
51
Design of Asymmetric Metal Catalysis
52
Future Prospects for Metal-catalyzed Asymmetric Synthesis
53
CV
of Masakatsu Shibasaki
54
CV
of Shigeki Matsunaga
54
Selected Publications
55
Catalytic Asymmetric Sulfur Ylide Mediated Epoxidation of Carbonyl Compounds
56
Varinder Aggarwal
Background
56
Results
57
Other Reactions of Sulfur Ylides from the Aggarwal Group
59
Conclusions and Future Perspectives
59
CV
of Varinder Aggarwal
60
Selected Publications
61
XII Contents
Asymmetrie Baeyer-Villiger
Reactions
62
Carsten Bolm
Background
62
Strategy
63
Results
64
Other Research Topics from the Bolm Group
65
CV
of
Carsten Bolm 65
Selected Publications
66
Planar Chiral Ligands Based on p^JParacyclophanes
67
Stefan
Bräse
Background
67
Strategy
68
Results
69
Application for the Synthesis of Natural Products
70
Other Asymmetric Syntheses from the
Bräse
Group
70
Conclusions and Future Perspectives
71
CV
of Stefan
Bräse 71
Selected Publications
71
Asymmetric Syntheses of S-jtrans^-NitrocydopropylJalanine
and S-jtrans^-AminocydopropylJalanine
72
Armin de
Majere
ană
Oleg V. Larionov
Background
72
Strategy and Results
73
Outlook
75
CV
of
Armin de
Meijere
75
CV
of
Oleg V
Larionov
76
Selected Publications
76
Copper-Bisjoxazoline) Catalyzed Synthesis of
ß-Lactams -
Enantioseiective Reaction of Alkynes with Nitrones
77
David A. Evans,
Florian
Kleinbeck and Magnus
Rüping
Background
77
Results
78
Summary
80
CV
of David A. Evans
81
CV
of Magnus
Rüping 82
CV
of
Florian
Kleinbeck
81
Selected Publications
81
Contents
XIII
Catalytic Asymmetric Conjugate Addition Reactions of Organometallic Reagents
83
Fernando
López
and Ben L.
Veringa
Background
83
The First Catalytic Enantioselective Approaches
83
Results
84
Cu-catalyzed Enantioselective CA of Organozinc Reagents
84
Highly Enantioselective Cu-catalyzed CA of Grignard Reagents
86
Conclusion and Future Perspectives
87
CV
of Fernando
López
87
CV
of Ben L. Feringa
88
Selected Publications
88
Catalytic Asymmetric Synthesis of Allylic Alcohols via Dynamic Kinetic Resolution
90
Hans-Joachim
Gais
Introduction
90
Strategy
91
Results
91
Application to the Synthesis of Natural Products
94
Other Asymmetric Syntheses from the
Gais
Group
94
Conclusion and Future Perspectives
94
CV
of Hans-Joachim
Gais
94
Selected Publications
95
Asymmetric Cross-coupling Reactions
97
Tamio Hayashi
Background
97
Results
97
Asymmetric Cross-coupling of Secondary
Alkyl
Grignard Reagents
97
Asymmetric Cross-Coupling Forming Axially Chiral Biaryls
99
Conclusions and Future Perspectives
100
CV
of Tamio Hayashi
101
Selected Publications
101
Asymmetric Allylic Substitutions
102
Günter Heimchen
Background
102
Results
103
Pd-Catalyzed Aliylic Substitutions
103
ir-Catalyzed Allylic Substitutions
104
Application for the Synthesis of Biologically Active Compounds
104
Other Asymmetric Syntheses from the
Helmchen
Group
205
Conclusions and Future Perspectives
105
CV
of
Günter Helmchen 105
Selected Publications
106
XIV Contents
Asymmetrie Homoatdol
Reactions
107
Dieter Hoppe
Background
107
Results
208
Enantioselective Additions via Stereospecific Deprotonation
108
Enantìoselectìve
Additions via (-J-Sparteine-mediated ct-Deprotonations
109
Enantioselective
γ
-Deprotonations
110
Synthetic Applications
110
CV
of Dieter
Hoppe 22 2
Selected Publications
222
Asymmetric Vinylogous Mukaiyama Aldol Reaction
222
Markus Katesse
and Jorma
Hassfeld
Introduction
222
Results
112
Conclusions and Further Perspectives
225
CV
of
Markus Kaiesse 116
CV
of Jorma
Hassfeld 2 2
б
Selected Publications
226
Chiral Lewis Acid Catalysis in Aqueous Media
117
Shu Kobayashi and Chikako Ogawa
Background
227
Results
117
Water-compatible Lewis Acid
227
Asymmetric Aldol Reactions
228
Asymmetric Hydroxymethylatkm Reactions
229
Asymmetric Mannich-type Reactions
220
CV
of Shu Kobayashi
222
CV
of Chikako Ogawa
222
Selected Publications
222
Asymmetric Epoxidation of Non-activated Olefins
123
Kazuhiro Matsumoto and Tsutomu Katsuki
Introduction
223
Results
223
Manganese(salen)
Catalyst
223
Ruthenium(salen) Catalyst
224
Titanium(salalen) Catalyst
225
Conclusion
126
CV
of Tsutomu Katsuki
227
CV
of Kazuhiro Matsumoto
127
Selected Publications
227
Contents
XV
Chiral Carbonyl Lewis
Acid
Complexes
in Asymmetrie
Syntheses
128
Keiji Maruoka and Takashi Ooi
Background
128
Results
128
Conclusions and Future Perspectives
131
CV
of Keiji Maruoka
131
CV
of Takashi
Ooi
131
Selected Publications
132
ZACA Reaction: Zr-catalyzed Asymmetric Carboalumination of Alkenes
133
Ei-ichi Negishi, Bo Liang,
Tibor
Novak and Ze Tan
Background and Discovery
133
Results
134
ZACA-Pd-catalyzed Cross-coupling Tandem Processes
for the Synthesis of Deoxypolypropionates and Related Compounds
134
Synthesis of
2
-Methyl- or
2-Eťhyl-l-alkanols
Not Readily
Purifiable by Chromatography or Recrystallization
137
CV
of Ei-ichi Negishi
137
Selected Publications
138
Bisoxazolines
-
a Privileged Ligand Class for Asymmetric Catalysis
139
Andreas Pfaltz
Background
139
Results
140
Semicorrins
140
C2 -Symmetric Bisoxazolines
140
Boron-bridged Bisoxazolines
142
Conclusion
142
CV
of Andreas Pfaltz
142
Selected Publications
143
Enantioselective
Cycloaddition
Reactions Catalyzed by Hydrogen Bonding
144
Viresh H. Rawal and Avinash
N.
Thadani
Background
144
Strategy
146
Results
146
Application to Other Reactions
147
Conclusions and Future Perspectives
147
CV
of Viresh H. Rawal
147
Selected Publications
148
XVI Contents
Direct
Catalytic Asymmetric Aldol-Tishchenko Reaction
149
Masakatsu Shibasaki and Takashi Ohshima
Background
349
Strategy
150
Results
150
Mechanistic Studies
152
Conclusions and Future Perspectives
253
CV
of Masakatsu Shibasaki
153
CV
of Takashi Ohshima
153
Selected Publications
154
Asymmetric Heck and other Palladium-catalyzed Reactions
155
Lutz F. Tietze
and
Florian Lotz
Background
155
Enantioselective Heck Reactions with Allylsilanes as the Alkene Component
155
CV
of
Lutz F.
Tietze
159
CV
of
Florian Lotz 159
Selected Publications
160
Asymmetric Catalysis with Chiral Acid
162
Hisashi Yamamoto
Background
161
Results
162
C2 Symmetric Chiral Lewis Acid Catalysts
162
Combined Acid Catalyst
162
CV
of Hisashi Yamamoto
165
Selected Publications
165
Part III Biocatalysis and Organocatalysis:
Asymmetric Synthesis Inspired by Nature
Introductory Chapter
169
Benjamin List
Introduction
169
The Aldol Reaction as an Example
269
Asymmetric Chemical Aldolizations
170
Conclusions and Outlook
172
CV
of Benjamin List
173
Selected Publications
173
Contents XVII
Enantioselective Photochemical
Reactions
174
Thorsten Bach
Background
174
Concept
175
Results
175
Perspectives
176
CV
of
Thorsten Bach 178
Selected Publications
178
Asymmetric Catalysis via Dynamic Kinetic Resolution
179
Jan
-Е.
Bäckvall
Background
179
Combined Enzyme and Metal Catalysis for Efficient
DKR
180
Results
180
Extension to
DKR
of Amines
182
Conclusions and Future Perspectives
183
CVofJan-E.
Bäckvall
183
Selected Publications
183
Catalytic Asymmetric Epoxidation of Enones and Related Compounds
185
Mbrecht
Berkessel
General
185
Electrophffic Catalytic Epoxidation
186
Nucleophilic Catalytic Epoxidation
186
Conclusions and Future Perspectives
188
CV
of
Albrecht Berkessel
188
Selected Publications
189
Kinetic Investigations of the
Soai Autocatalytic
Reaction
190
Donna G.
Blackmona
Background
190
Kinetic Studies using Reaction Calorimetry
191
CV
of Donna G.
Blackmond 194
Selected Publications
194
Planar-chiral Heterocycles as Enantioselective Organocatalysts
195
Gregory C.
Fu
Background and Design
295
Applications
195
Conclusions and Future Perspectives
199
CV
of Gregory
С
Fu
199
Selected Publications
199
XVIII Contents
An Organocatalytic
Approach to Optically Active Six-membered Rings
200
Karl Anker j0rgensen
Background
200
Strategy
201
Results
202
Synthesis of
γ-
and E-lactones
204
Conclusions and Future Perspectives
204
CV
of Karl Anker Jargensen
204
Selected Publications
205
Non-linear Effects in Asymmetric Catalysis
206
Henri B.
Kagan
Background
206
Enantiomerically Impure Chiral Auxiliaries
206
Non-linear Effects
206
Results
207
Examples of Asymmetric Amplifications
207
Kinetic Models
208
Applications of Non-linear Effects
209
Conclusion and Perspectives
209
CV
of Henri B.
Kagan
209
Selected Publications
210
Asymmetric Organocatalysis
211
Steven V. Ley
Background
223
Results
212
Conclusions and Future Perspectives
216
CV
of Steven V. Ley
236
Selected Publications
236
Directed Evolution of Enzymes for Asymmetric Syntheses
237
Manfred T. Reetz
Background
217
Strategy and Early Results
237
Generalizing the Concept
239
New Strategies
219
Conclusions and Perspectives
220
CV
of Manfred T. Reetz
220
Selected Publications
221
Contents XIX
Asymmetrie Autocatalysis
and Its Implications in the Origin
of Chiral Homogeneity of Biomolecules
222
Kenso
Soai
and Tsuneomi Kawasaki
Background
222
Results
223
Chiral Amplification by Asymmetric Autocatalysis 22i
Asymmetric Autocatalysis as a link Between the Origin
of Chirality and Highly Enantioenriched Molecules
223
Spontaneous Absolute Asymmetric Synthesis
224
Conclusions and Future Perspectives
226
CV
of Kenso
Soai
226
CV
of Tsuneomi Kawasaki
227
Selected Publications
227
Asymmetric Synthesis using Deoxyribose-5-phosphate Aldolase
228
Chi-Huey Wong and William A.
Greenberg
Background
228
Results
229
Catalytic Mechanism
229
Synthetic Applications
229
Application to the Synthesis of Epothilones and Statins
230
Conclusion
231
CV
of Chi-Huey Wong
232
CV
of William A.
Greenberg
232
Selected Publications
232
Part IV Asymmetric Reactions in Total Synthesis
Introductory Chapter
235
К. С
Nicolaou and Paul G. Bulger
Background
235
Reactions
235
Aldol
235
Alkylation
237
Diels-Alder
239
Allylation
240
Palladium-catalyzed Cross-coupling
241
Epoxidation
244
Dihydroxylation/ammohydroxylation
247
Organocatalytic Reductions
248
Metal-catalyzed
Hydrogénations
248
Enzymatic
250
Conclusions
250
CV
of
К. С
Nicolaou
251
CV
of Paul G. Bulger
251
Selected Publications
252
XX
Contents
Ring Rearrangement Metathesis (RRM) in Alkaloid Synthesis
254
Nicole
Holub
and Siegfried Blechert
Background and Strategy
254
Results
255
Tetraponerines
255
Tra»s-195A
256
Lasubine II
256
Astrophylline and Dendrochrysine
257
Conclusions and Future Perspectives 25S
CV
of Siegfried Blechert
259
Selected Publications
259
Asymmetric Synthesis of Biaryls by the Lactone Method
260
Gerhard
Bringmann, Tanja
Gulder
and Tobias
A. M. Guider
Introduction
260
The Basic Concept of the Lactone Method
260
Application of the Lactone Concept to Natural Product Synthesis
261
Conclusions and Further Perspectives
263
CV
of Gerhard
Bringmann 263
Selected Publications
264
Asymmetric Synthesis of Merrilactone A
265
Samuel
J
.
Danishefsky
Background
265
Synthetic Strategy
265
Synthesis of Merrilactone A
267
CV
of Samuel J. Danishefsky
269
Selected Publications
270
Asymmetric Synthesis of Cyclic Ketal
and Spiroaminal-containing Natural Products
272
Craig
J
.
Forsyth
Background
271
Results
272
Okadaic Acid
-
Three Spiroketalization Methods
272
Additional Ketals via Double Intramolecular
Hetero
Michael Additions
273
Synthesis of the Azaspiracid Spiroaminal
274
Conclusion and Future Perspectives
275
CV
of Craig J.
Forsyth
275
Selected Publications
276
Contents XXI
Case Studies at the Metathesis/Asymmetric Synthesis Interface
277
Mois
Fürstner
Background
277
Results
277
(-(-Gloeosporone
277
(-J-Isooncinotíne
279
Conclusions and Future Perspectives
281
CV
of Alois
Fürstner 281
Selected Publications
281
Asymmetric Synthesis of
Amino
Acids by Rhodium and Ruthenium Catalysis
282
Jean Pierre Genet
Introduction
282
Asymmetric
Hydrogénation
Reactions
282
Chiral Diphosphine ligands and Diversity of Chiral Ru Catalysts
283
Results
283
Asymmetric
Hydrogénation
of Dehydroamino Acids
283
Asymmetric Syntheses of a-Amino
ß-Hydroxy
Acids
(DKR)
284
Asymmetric Syntheses of Natural Products
285
Tandem-1,4
addition/Enantioselective
Protonation
Catalyzed by Rhodium
285
Conclusions
286
CV
of Jean Pierre Genet
286
Selected Publications
287
Asymmetric Syntheses of Pheromones
288
Kenji Mori
Background
288
Strategy and Results
288
Derivation from Optically Active Starting Materials
289
Enantiomer Separation
289
Asymmetric Synthesis
290
Conclusion and Future Perspective
292
CV
of Kenji Mori
292
Selected Publications
292
Total Synthesis of Polyketides Using Asymmetric Aldol Reactions
293
Ian Paterson
Background
293
Results
294
Stereocontrol in the Boron Aldol Reactions of Ketones
294
Application to the Total Synthesis of Altohyrtm A (Spongistatin
1) 296
Conclusions and Future Perspectives
296
CV
of Ian Paterson
296
Selected Publications
298
XXII Contents
Asymmetrie
Synthesis on the Solid Phase
299
Torben Leßmann
and Herbert
Waldmann
Introduction
299
Results
299
Asymmetric Aldol Reactions
299
Asymmetric
Cycloadditions
300
Asymmetric
Epoxide
Openings
302
Other Reactions
302
Conclusion
302
CV
of Herbert
Waldmann 302
CV
of
Torben Leßmann 303
Selected Publications
303
Part V Asymmetric Synthesis in Industry
Introductory Chapter
307
Herbert Hugl
Background
307
Industrial Production of Chiral Compounds
307
Outlook
310
CV
of Herbert Hugl
310
Selected Publications
310
Industrial Application of Enantioselective Catalysis
311
Hans-Ulrich Blaser
The Potential of Enantioselective Catalysis
311
Hurdles on the Way to an Industrial Process
311
Catalyst Performance
312
Availability and Cost of the Catalyst
312
Development Time
313
Selected Milestones in Industrial Application
333
Conclusions and Future Perspectives
315
CV
of
Hans-Ulrich Blaser 315
Selected Publications
315
Crystallization-Induced Diastereoselection for the Synthesis of Aprepitant
326
J. Brands, P. Pye and K.
Rossen
Background
316
Results
317
Bicydic Acetal Approach
317
Lactam
Approach
318
Conclusion
320
CV
of
Karel
M.
Jos Brands
320
CV
of Philip Pye
320
CV
of
Kai Rossen 320
Selected Publications
321
Contents XXIII
Combinatorial Methods in Asymmetric Syntheses
322
Stefan Dahrnen
Background
322
Results
322
Ligand Screening
322
Additive Screening
324
Arylzinc Precursors
324
CV
of Stefan Dahmen
326
Selected Publications
326
Biocatalytic Production of Optically Active Amines
327
Klaus Ditrich
Background
327
Results
327
Conclusions and Future Perspectives
331
CV
of Klaus Ditrich
331
Selected Publications
331
The Monsanto L-Dopa Process
332
William S. Knowles
Background
332
i-DOPA Process
332
Other Industrial Applications
335
Conclusions
335
CV
of William S. Knowles
335
Selected Publications
336
Asymmetric
Hydrogénation
through Metal-Ligand Bifunctional Catalysis
337
Ryoji Noyori, Takeshi Ohkuma, Christian A.
Sandoval
and
Kilián
Muñiz
Background
337
Strategy
337
Results
337
Catalytic Cycle
339
CV
of Ryoji Noyori
340
Selected Publications
341
XXIV Contents
Many Ways are Leading to Rome
-
Today s Variety of Competing Synthetic Methods in Industry
342
Andreas Job and Andreas
Stolle
Introduction
342
Synthetic Concepts
343
Biochemical Approach
344
Catalytic
Hydrogénation
Approach
345
Chiral Pool Synthesis
345
Conclusion
346
CV
of Andreas Job
346
CV
of Andreas
Stolle 346
Selected Publications
347
Author Index
349
Subject Index
352
This Who s who of asymmetric synthesis introduces the reader
to the leaders in the field with a four-page concentrate of their area of
research along with a short biography. The book is organized into
five chapters, each with an introductory preface. Starting from the key
concepts of asymmetric synthesis (diastereoselective methods, asym¬
metric catalysis) the focus then shifts to its application to the synthesis
natural products and industrial processes
Graduate students, academic and industrial researchers will find
this book a rich source of inspiration for their own work as well as
an indispensable tool for the preparation of seminars and exams.
A must for everyone in the field.
Mat/lias
Christmann
was born in
Peiné,
beated
¡η
Lower Saxony,
Germany,
in
197г,
He studied Chemistry in
Braunschweig
figgj—199SJ
and Hannover
figgS-sooîj
and obtained his doctorate under the guidance of
Markus
Kalesse. After a postdoctoral appointment with CraigJ.
Forsyth
at the University of Minnesota
(1001-2002),
he
began his independent research career associated with
Dieter Enders
at the RWTH Aachen in 200J, His research
interests include organocatalysis and natural product
synthesis.
SUfiin
Bräst,
born in Kiel,
Germany
in
1967,
studied
chemistry in
Göttingen, Bangor
(UK) and Marseille. He
obtained his
doctorats
¡η
iggj under the guidance of
Armin de
Meijere in
Göttingen.
After postdoctoral appoint¬
ments at Uppsala University
(Jan Bäckvall)
and The Scripps
Research Institute
(К.
C. Nicolaou), he began his independ¬
ent research career at the RWTH Aachen associated with
Dieter
Enders
¡η
1997
and finished his
Habilitation in
3001.
He became Professor at the
University
of Bonn that
same year and Full Professor of Organic Chemistry at the
Technical University of Karlsruhe
m
2003.
His research
interests include asymmetric metal-catalyzed processes
and combinatorial chemistry towards the synthesis of bio¬
logically active compounds.
|
| adam_txt |
IX
Contents
Foreword V
Message from the Editors
XXV
List of Abbreviations
XXVII
Named and Unnamed Reactions
XXXI
List of Contributors
XXXIII
Part I Chiral Auxiliaries in Asymmetric Synthesis
Introductory Chapter
3
David A. Evans,
Günter Helmchen
and Magnus Raping
Background
3
Results
4
Summary
7
CV
of David A. Evans
8
CV
of
Günter Helmchen
S
CV
of Magnus
Rüping 9
Selected Publications
9
Asymmetric Epoxidation of Pentadienols
10
Reinhard
Bruckner
Background
10
Objective: Making Building Blocks for the
Synthesis of
1,3,5,7,—
-Polyols from Epoxyalcohols
11
Results
12
Asymmetric Epoxidation of a Conjugated Pentadienol
12
Asymmetric Epoxidation of a Nonconjugated Pentadienol
13
CV
of
Reinhard
Bruckner IS
Selected Publications
16
X
Contents
Asymmetrie
Synthesis using Sulfur-Nitrogen Reagents
17
Franklin A. Davis
Background
17
Results
17
Asymmetric Oxidations using N-Sulfonyloxaziridines
17
Asymmetric Fluorination of Enolates with N-Fluoro^lO-Camphorsultams
19
Asymmetric Synthesis of
Amine
Derivatives using
Enantiopure Sulfinimines (N-Sulfinyl Imines)
19
Outlook
20
CV
of Franklin A. Davis
20
Selected Publications
22
Asymmetric Syntheses with
SAMP^RAMP-Hydrazones
23
Dieter
Enders
and Wolfgang Bettray
Background
23
Strategy
24
Results
25
Application for the Synthesis of Natural Products
26
Other Asymmetric Syntheses from the
Enders
Group
27
Conclusions and Future Perspectives
27
CV
of Dieter
Enders 27
Selected Publications
28
Asymmetric Allylation Reactions
29
Reinhard W.
Hoffmann
Background
29
Results
29
Type (I) Allylmetallation of Aldehydes
29
Second Generation Allylmetallation Reagents
31
CV
of
Reinhard W.
Hoffmann
32
Selected Publications
33
Carbohydrates as Chirai Auxiliaries
34
Horst Kunz
Introduction
34
Results
34
Carbohydrate Auxiliaries in
Cycloaddition
Reactions
34
Conjugate Addition Reactions Directed by Carbohydrate Auxiliaries
35
Glycosylamines in Stereoselective Synthesis
36
Conclusions
38
CV
of
Horst Kunz 38
Selected Publications
38
Contents
XI
The Use of Chiral Oxazolines in early
C
-С
Bond Forming Reactions
39
Albert I. Meyers
Background
39
Results
40
CV
of Albert I. Meyers
41
Selected Publications
41
Asymmetric Synthesis of Amines and
Amino
Acids from Amines
42
Shun-Ichi Murahashi and Yasushi
Imada
Background
42
Strategy
43
Results
43
Diastereoselective Reactions of Nitrones
43
Enantioselective Reactions of Nitrones
44
Conclusions and Future Perspectives
46
CV
of Shun-Ichi Murahashi
46
Selected Publications
47
Part II Metal-catalyzed Asymmetric Synthesis
Introductory Chapter
51
Masakatsu Shibasaki and Shigeki Matsunaga
Introduction
51
Design of Asymmetric Metal Catalysis
52
Future Prospects for Metal-catalyzed Asymmetric Synthesis
53
CV
of Masakatsu Shibasaki
54
CV
of Shigeki Matsunaga
54
Selected Publications
55
Catalytic Asymmetric Sulfur Ylide Mediated Epoxidation of Carbonyl Compounds
56
Varinder Aggarwal
Background
56
Results
57
Other Reactions of Sulfur Ylides from the Aggarwal Group
59
Conclusions and Future Perspectives
59
CV
of Varinder Aggarwal
60
Selected Publications
61
XII Contents
Asymmetrie Baeyer-Villiger
Reactions
62
Carsten Bolm
Background
62
Strategy
63
Results
64
Other Research Topics from the Bolm Group
65
CV
of
Carsten Bolm 65
Selected Publications
66
Planar Chiral Ligands Based on p^JParacyclophanes
67
Stefan
Bräse
Background
67
Strategy
68
Results
69
Application for the Synthesis of Natural Products
70
Other Asymmetric Syntheses from the
Bräse
Group
70
Conclusions and Future Perspectives
71
CV
of Stefan
Bräse 71
Selected Publications
71
Asymmetric Syntheses of S-jtrans^-NitrocydopropylJalanine
and S-jtrans^-AminocydopropylJalanine
72
Armin de
Majere
ană
Oleg V. Larionov
Background
72
Strategy and Results
73
Outlook
75
CV
of
Armin de
Meijere
75
CV
of
Oleg V
Larionov
76
Selected Publications
76
Copper-Bisjoxazoline) Catalyzed Synthesis of
ß-Lactams -
Enantioseiective Reaction of Alkynes with Nitrones
77
David A. Evans,
Florian
Kleinbeck and Magnus
Rüping
Background
77
Results
78
Summary
80
CV
of David A. Evans
81
CV
of Magnus
Rüping 82
CV
of
Florian
Kleinbeck
81
Selected Publications
81
Contents
XIII
Catalytic Asymmetric Conjugate Addition Reactions of Organometallic Reagents
83
Fernando
López
and Ben L.
Veringa
Background
83
The First Catalytic Enantioselective Approaches
83
Results
84
Cu-catalyzed Enantioselective CA of Organozinc Reagents
84
Highly Enantioselective Cu-catalyzed CA of Grignard Reagents
86
Conclusion and Future Perspectives
87
CV
of Fernando
López
87
CV
of Ben L. Feringa
88
Selected Publications
88
Catalytic Asymmetric Synthesis of Allylic Alcohols via Dynamic Kinetic Resolution
90
Hans-Joachim
Gais
Introduction
90
Strategy
91
Results
91
Application to the Synthesis of Natural Products
94
Other Asymmetric Syntheses from the
Gais
Group
94
Conclusion and Future Perspectives
94
CV
of Hans-Joachim
Gais
94
Selected Publications
95
Asymmetric Cross-coupling Reactions
97
Tamio Hayashi
Background
97
Results
97
Asymmetric Cross-coupling of Secondary
Alkyl
Grignard Reagents
97
Asymmetric Cross-Coupling Forming Axially Chiral Biaryls
99
Conclusions and Future Perspectives
100
CV
of Tamio Hayashi
101
Selected Publications
101
Asymmetric Allylic Substitutions
102
Günter Heimchen
Background
102
Results
103
Pd-Catalyzed Aliylic Substitutions
103
ir-Catalyzed Allylic Substitutions
104
Application for the Synthesis of Biologically Active Compounds
104
Other Asymmetric Syntheses from the
Helmchen
Group
205
Conclusions and Future Perspectives
105
CV
of
Günter Helmchen 105
Selected Publications
106
XIV Contents
Asymmetrie Homoatdol
Reactions
107
Dieter Hoppe
Background
107
Results
208
Enantioselective Additions via Stereospecific Deprotonation
108
Enantìoselectìve
Additions via (-J-Sparteine-mediated ct-Deprotonations
109
Enantioselective
γ
-Deprotonations
110
Synthetic Applications
110
CV
of Dieter
Hoppe 22 2
Selected Publications
222
Asymmetric Vinylogous Mukaiyama Aldol Reaction
222
Markus Katesse
and Jorma
Hassfeld
Introduction
222
Results
112
Conclusions and Further Perspectives
225
CV
of
Markus Kaiesse 116
CV
of Jorma
Hassfeld 2 2
б
Selected Publications
226
Chiral Lewis Acid Catalysis in Aqueous Media
117
Shu Kobayashi and Chikako Ogawa
Background
227
Results
117
Water-compatible Lewis Acid
227
Asymmetric Aldol Reactions
228
Asymmetric Hydroxymethylatkm Reactions
229
Asymmetric Mannich-type Reactions
220
CV
of Shu Kobayashi
222
CV
of Chikako Ogawa
222
Selected Publications
222
Asymmetric Epoxidation of Non-activated Olefins
123
Kazuhiro Matsumoto and Tsutomu Katsuki
Introduction
223
Results
223
Manganese(salen)
Catalyst
223
Ruthenium(salen) Catalyst
224
Titanium(salalen) Catalyst
225
Conclusion
126
CV
of Tsutomu Katsuki
227
CV
of Kazuhiro Matsumoto
127
Selected Publications
227
Contents
XV
Chiral Carbonyl Lewis
Acid
Complexes
in Asymmetrie
Syntheses
128
Keiji Maruoka and Takashi Ooi
Background
128
Results
128
Conclusions and Future Perspectives
131
CV
of Keiji Maruoka
131
CV
of Takashi
Ooi
131
Selected Publications
132
ZACA Reaction: Zr-catalyzed Asymmetric Carboalumination of Alkenes
133
Ei-ichi Negishi, Bo Liang,
Tibor
Novak and Ze Tan
Background and Discovery
133
Results
134
ZACA-Pd-catalyzed Cross-coupling Tandem Processes
for the Synthesis of Deoxypolypropionates and Related Compounds
134
Synthesis of
2
-Methyl- or
2-Eťhyl-l-alkanols
Not Readily
Purifiable by Chromatography or Recrystallization
137
CV
of Ei-ichi Negishi
137
Selected Publications
138
Bisoxazolines
-
a Privileged Ligand Class for Asymmetric Catalysis
139
Andreas Pfaltz
Background
139
Results
140
Semicorrins
140
C2 -Symmetric Bisoxazolines
140
Boron-bridged Bisoxazolines
142
Conclusion
142
CV
of Andreas Pfaltz
142
Selected Publications
143
Enantioselective
Cycloaddition
Reactions Catalyzed by Hydrogen Bonding
144
Viresh H. Rawal and Avinash
N.
Thadani
Background
144
Strategy
146
Results
146
Application to Other Reactions
147
Conclusions and Future Perspectives
147
CV
of Viresh H. Rawal
147
Selected Publications
148
XVI Contents
Direct
Catalytic Asymmetric Aldol-Tishchenko Reaction
149
Masakatsu Shibasaki and Takashi Ohshima
Background
349
Strategy
150
Results
150
Mechanistic Studies
152
Conclusions and Future Perspectives
253
CV
of Masakatsu Shibasaki
153
CV
of Takashi Ohshima
153
Selected Publications
154
Asymmetric Heck and other Palladium-catalyzed Reactions
155
Lutz F. Tietze
and
Florian Lotz
Background
155
Enantioselective Heck Reactions with Allylsilanes as the Alkene Component
155
CV
of
Lutz F.
Tietze
159
CV
of
Florian Lotz 159
Selected Publications
160
Asymmetric Catalysis with Chiral Acid
162
Hisashi Yamamoto
Background
161
Results
162
C2 Symmetric Chiral Lewis Acid Catalysts
162
Combined Acid Catalyst
162
CV
of Hisashi Yamamoto
165
Selected Publications
165
Part III Biocatalysis and Organocatalysis:
Asymmetric Synthesis Inspired by Nature
Introductory Chapter
169
Benjamin List
Introduction
169
The Aldol Reaction as an Example
269
Asymmetric Chemical Aldolizations
170
Conclusions and Outlook
172
CV
of Benjamin List
173
Selected Publications
173
Contents XVII
Enantioselective Photochemical
Reactions
174
Thorsten Bach
Background
174
Concept
175
Results
175
Perspectives
176
CV
of
Thorsten Bach 178
Selected Publications
178
Asymmetric Catalysis via Dynamic Kinetic Resolution
179
Jan
-Е.
Bäckvall
Background
179
Combined Enzyme and Metal Catalysis for Efficient
DKR
180
Results
180
Extension to
DKR
of Amines
182
Conclusions and Future Perspectives
183
CVofJan-E.
Bäckvall
183
Selected Publications
183
Catalytic Asymmetric Epoxidation of Enones and Related Compounds
185
Mbrecht
Berkessel
General
185
Electrophffic Catalytic Epoxidation
186
Nucleophilic Catalytic Epoxidation
186
Conclusions and Future Perspectives
188
CV
of
Albrecht Berkessel
188
Selected Publications
189
Kinetic Investigations of the
Soai Autocatalytic
Reaction
190
Donna G.
Blackmona
Background
190
Kinetic Studies using Reaction Calorimetry
191
CV
of Donna G.
Blackmond 194
Selected Publications
194
Planar-chiral Heterocycles as Enantioselective Organocatalysts
195
Gregory C.
Fu
Background and Design
295
Applications
195
Conclusions and Future Perspectives
199
CV
of Gregory
С
Fu
199
Selected Publications
199
XVIII Contents
An Organocatalytic
Approach to Optically Active Six-membered Rings
200
Karl Anker j0rgensen
Background
200
Strategy
201
Results
202
Synthesis of
γ-
and E-lactones
204
Conclusions and Future Perspectives
204
CV
of Karl Anker Jargensen
204
Selected Publications
205
Non-linear Effects in Asymmetric Catalysis
206
Henri B.
Kagan
Background
206
Enantiomerically Impure Chiral Auxiliaries
206
Non-linear Effects
206
Results
207
Examples of Asymmetric Amplifications
207
Kinetic Models
208
Applications of Non-linear Effects
209
Conclusion and Perspectives
209
CV
of Henri B.
Kagan
209
Selected Publications
210
Asymmetric Organocatalysis
211
Steven V. Ley
Background
223
Results
212
Conclusions and Future Perspectives
216
CV
of Steven V. Ley
236
Selected Publications
236
Directed Evolution of Enzymes for Asymmetric Syntheses
237
Manfred T. Reetz
Background
217
Strategy and Early Results
237
Generalizing the Concept
239
New Strategies
219
Conclusions and Perspectives
220
CV
of Manfred T. Reetz
220
Selected Publications
221
Contents XIX
Asymmetrie Autocatalysis
and Its Implications in the Origin
of Chiral Homogeneity of Biomolecules
222
Kenso
Soai
and Tsuneomi Kawasaki
Background
222
Results
223
Chiral Amplification by Asymmetric Autocatalysis 22i
Asymmetric Autocatalysis as a link Between the Origin
of Chirality and Highly Enantioenriched Molecules
223
Spontaneous Absolute Asymmetric Synthesis
224
Conclusions and Future Perspectives
226
CV
of Kenso
Soai
226
CV
of Tsuneomi Kawasaki
227
Selected Publications
227
Asymmetric Synthesis using Deoxyribose-5-phosphate Aldolase
228
Chi-Huey Wong and William A.
Greenberg
Background
228
Results
229
Catalytic Mechanism
229
Synthetic Applications
229
Application to the Synthesis of Epothilones and Statins
230
Conclusion
231
CV
of Chi-Huey Wong
232
CV
of William A.
Greenberg
232
Selected Publications
232
Part IV Asymmetric Reactions in Total Synthesis
Introductory Chapter
235
К. С
Nicolaou and Paul G. Bulger
Background
235
Reactions
235
Aldol
235
Alkylation
237
Diels-Alder
239
Allylation
240
Palladium-catalyzed Cross-coupling
241
Epoxidation
244
Dihydroxylation/ammohydroxylation
247
Organocatalytic Reductions
248
Metal-catalyzed
Hydrogénations
248
Enzymatic
250
Conclusions
250
CV
of
К. С
Nicolaou
251
CV
of Paul G. Bulger
251
Selected Publications
252
XX
Contents
Ring Rearrangement Metathesis (RRM) in Alkaloid Synthesis
254
Nicole
Holub
and Siegfried Blechert
Background and Strategy
254
Results
255
Tetraponerines
255
Tra»s-195A
256
Lasubine II
256
Astrophylline and Dendrochrysine
257
Conclusions and Future Perspectives 25S
CV
of Siegfried Blechert
259
Selected Publications
259
Asymmetric Synthesis of Biaryls by the 'Lactone Method'
260
Gerhard
Bringmann, Tanja
Gulder
and Tobias
A. M. Guider
Introduction
260
The Basic Concept of the 'Lactone Method'
260
Application of the 'Lactone Concept to Natural Product Synthesis
261
Conclusions and Further Perspectives
263
CV
of Gerhard
Bringmann 263
Selected Publications
264
Asymmetric Synthesis of Merrilactone A
265
Samuel
J
.
Danishefsky
Background
265
Synthetic Strategy
265
Synthesis of Merrilactone A
267
CV
of Samuel J. Danishefsky
269
Selected Publications
270
Asymmetric Synthesis of Cyclic Ketal
and Spiroaminal-containing Natural Products
272
Craig
J
.
Forsyth
Background
271
Results
272
Okadaic Acid
-
Three Spiroketalization Methods
272
Additional Ketals via Double Intramolecular
Hetero
Michael Additions
273
Synthesis of the Azaspiracid Spiroaminal
274
Conclusion and Future Perspectives
275
CV
of Craig J.
Forsyth
275
Selected Publications
276
Contents XXI
Case Studies at the Metathesis/Asymmetric Synthesis Interface
277
Mois
Fürstner
Background
277
Results
277
(-(-Gloeosporone
277
(-J-Isooncinotíne
279
Conclusions and Future Perspectives
281
CV
of Alois
Fürstner 281
Selected Publications
281
Asymmetric Synthesis of
Amino
Acids by Rhodium and Ruthenium Catalysis
282
Jean Pierre Genet
Introduction
282
Asymmetric
Hydrogénation
Reactions
282
Chiral Diphosphine ligands and Diversity of Chiral Ru Catalysts
283
Results
283
Asymmetric
Hydrogénation
of Dehydroamino Acids
283
Asymmetric Syntheses of a-Amino
ß-Hydroxy
Acids
(DKR)
284
Asymmetric Syntheses of Natural Products
285
Tandem-1,4
addition/Enantioselective
Protonation
Catalyzed by Rhodium
285
Conclusions
286
CV
of Jean Pierre Genet
286
Selected Publications
287
Asymmetric Syntheses of Pheromones
288
Kenji Mori
Background
288
Strategy and Results
288
Derivation from Optically Active Starting Materials
289
Enantiomer Separation
289
Asymmetric Synthesis
290
Conclusion and Future Perspective
292
CV
of Kenji Mori
292
Selected Publications
292
Total Synthesis of Polyketides Using Asymmetric Aldol Reactions
293
Ian Paterson
Background
293
Results
294
Stereocontrol in the Boron Aldol Reactions of Ketones
294
Application to the Total Synthesis of Altohyrtm A (Spongistatin
1) 296
Conclusions and Future Perspectives
296
CV
of Ian Paterson
296
Selected Publications
298
XXII Contents
Asymmetrie
Synthesis on the Solid Phase
299
Torben Leßmann
and Herbert
Waldmann
Introduction
299
Results
299
Asymmetric Aldol Reactions
299
Asymmetric
Cycloadditions
300
Asymmetric
Epoxide
Openings
302
Other Reactions
302
Conclusion
302
CV
of Herbert
Waldmann 302
CV
of
Torben Leßmann 303
Selected Publications
303
Part V Asymmetric Synthesis in Industry
Introductory Chapter
307
Herbert Hugl
Background
307
Industrial Production of Chiral Compounds
307
Outlook
310
CV
of Herbert Hugl
310
Selected Publications
310
Industrial Application of Enantioselective Catalysis
311
Hans-Ulrich Blaser
The Potential of Enantioselective Catalysis
311
Hurdles on the Way to an Industrial Process
311
Catalyst Performance
312
Availability and Cost of the Catalyst
312
Development Time
313
Selected Milestones in Industrial Application
333
Conclusions and Future Perspectives
315
CV
of
Hans-Ulrich Blaser 315
Selected Publications
315
Crystallization-Induced Diastereoselection for the Synthesis of Aprepitant
326
J. Brands, P. Pye and K.
Rossen
Background
316
Results
317
Bicydic Acetal Approach
317
Lactam
Approach
318
Conclusion
320
CV
of
Karel
M.
Jos Brands
320
CV
of Philip Pye
320
CV
of
Kai Rossen 320
Selected Publications
321
Contents XXIII
Combinatorial Methods in Asymmetric Syntheses
322
Stefan Dahrnen
Background
322
Results
322
Ligand Screening
322
Additive Screening
324
Arylzinc Precursors
324
CV
of Stefan Dahmen
326
Selected Publications
326
Biocatalytic Production of Optically Active Amines
327
Klaus Ditrich
Background
327
Results
327
Conclusions and Future Perspectives
331
CV
of Klaus Ditrich
331
Selected Publications
331
The Monsanto L-Dopa Process
332
William S. Knowles
Background
332
i-DOPA Process
332
Other Industrial Applications
335
Conclusions
335
CV
of William S. Knowles
335
Selected Publications
336
Asymmetric
Hydrogénation
through Metal-Ligand Bifunctional Catalysis
337
Ryoji Noyori, Takeshi Ohkuma, Christian A.
Sandoval
and
Kilián
Muñiz
Background
337
Strategy
337
Results
337
Catalytic Cycle
339
CV
of Ryoji Noyori
340
Selected Publications
341
XXIV Contents
Many Ways are Leading to Rome
-
Today's Variety of Competing Synthetic Methods in Industry
342
Andreas Job and Andreas
Stolle
Introduction
342
Synthetic Concepts
343
Biochemical Approach
344
Catalytic
Hydrogénation
Approach
345
Chiral Pool Synthesis
345
Conclusion
346
CV
of Andreas Job
346
CV
of Andreas
Stolle 346
Selected Publications
347
Author Index
349
Subject Index
352
This "Who's who" of asymmetric synthesis introduces the reader
to the leaders in the field with a four-page concentrate of their area of
research along with a short biography. The book is organized into
five chapters, each with an introductory preface. Starting from the key
concepts of asymmetric synthesis (diastereoselective methods, asym¬
metric catalysis) the focus then shifts to its application to the synthesis
natural products and industrial processes
Graduate students, academic and industrial researchers will find
this book a rich source of inspiration for their own work as well as
an indispensable tool for the preparation of seminars and exams.
A must for everyone in the field.
Mat/lias
Christmann
was born in
Peiné,
beated
¡η
Lower Saxony,
Germany,
in
197г,
He studied Chemistry in
Braunschweig
figgj—199SJ
and Hannover
figgS-sooîj
and obtained his doctorate under the guidance of
Markus
Kalesse. After a postdoctoral appointment with CraigJ.
Forsyth
at the University of Minnesota
(1001-2002),
he
began his independent research career associated with
Dieter Enders
at the RWTH Aachen in 200J, His research
interests include organocatalysis and natural product
synthesis.
SUfiin
Bräst,
born in Kiel,
Germany
in
1967,
studied
chemistry in
Göttingen, Bangor
(UK) and Marseille. He
obtained his
doctorats
¡η
iggj under the guidance of
Armin de
Meijere in
Göttingen.
After postdoctoral appoint¬
ments at Uppsala University
(Jan Bäckvall)
and The Scripps
Research Institute
(К.
C. Nicolaou), he began his independ¬
ent research career at the RWTH Aachen associated with
Dieter
Enders
¡η
1997
and finished his
"Habilitation" in
3001.
He became Professor at the
University
of Bonn that
same year and Full Professor of Organic Chemistry at the
Technical University of Karlsruhe
m
2003.
His research
interests include asymmetric metal-catalyzed processes
and combinatorial chemistry towards the synthesis of bio¬
logically active compounds. |
| any_adam_object | 1 |
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| author_GND | (DE-588)122971035 |
| building | Verbundindex |
| bvnumber | BV023022614 |
| callnumber-first | Q - Science |
| callnumber-label | QD262 |
| callnumber-raw | QD262 |
| callnumber-search | QD262 |
| callnumber-sort | QD 3262 |
| callnumber-subject | QD - Chemistry |
| classification_rvk | VK 5500 |
| ctrlnum | (OCoLC)181925664 (DE-599)GBV525998624 |
| dewey-full | 547.2 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.2 |
| dewey-search | 547.2 |
| dewey-sort | 3547.2 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| discipline_str_mv | Chemie / Pharmazie |
| edition | 2., completely rev. ed. |
| format | Book |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV023022614 |
| illustrated | Illustrated |
| index_date | 2024-07-02T19:13:42Z |
| indexdate | 2024-07-09T21:09:12Z |
| institution | BVB |
| isbn | 9783527320936 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016226644 |
| oclc_num | 181925664 |
| open_access_boolean | |
| owner | DE-29T DE-355 DE-BY-UBR |
| owner_facet | DE-29T DE-355 DE-BY-UBR |
| physical | XL, 355 S. Ill., graph. Darst. |
| publishDate | 2008 |
| publishDateSearch | 2008 |
| publishDateSort | 2008 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Asymmetric synthesis the essentials ed. by Mathias Christmann and Stefan Bräse 2., completely rev. ed. Weinheim WILEY-VCH 2008 XL, 355 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Literaturangaben Chiraliteit gtt Enantiomeren gtt Stereochemie gtt Stereoselectiviteit gtt Synthese (chemie) gtt Asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Asymmetrische Synthese (DE-588)4135603-2 s DE-604 Christmann, Mathias 1972- Sonstige (DE-588)122971035 oth Bräse, Stefan Sonstige oth http://deposit.dnb.de/cgi-bin/dokserv?id=2774561&prov=M&dok_var=1&dok_ext=htm Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016226644&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016226644&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext |
| spellingShingle | Asymmetric synthesis the essentials Chiraliteit gtt Enantiomeren gtt Stereochemie gtt Stereoselectiviteit gtt Synthese (chemie) gtt Asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd |
| subject_GND | (DE-588)4135603-2 (DE-588)4143413-4 |
| title | Asymmetric synthesis the essentials |
| title_auth | Asymmetric synthesis the essentials |
| title_exact_search | Asymmetric synthesis the essentials |
| title_exact_search_txtP | Asymmetric synthesis the essentials |
| title_full | Asymmetric synthesis the essentials ed. by Mathias Christmann and Stefan Bräse |
| title_fullStr | Asymmetric synthesis the essentials ed. by Mathias Christmann and Stefan Bräse |
| title_full_unstemmed | Asymmetric synthesis the essentials ed. by Mathias Christmann and Stefan Bräse |
| title_short | Asymmetric synthesis |
| title_sort | asymmetric synthesis the essentials |
| title_sub | the essentials |
| topic | Chiraliteit gtt Enantiomeren gtt Stereochemie gtt Stereoselectiviteit gtt Synthese (chemie) gtt Asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd |
| topic_facet | Chiraliteit Enantiomeren Stereochemie Stereoselectiviteit Synthese (chemie) Asymmetric synthesis Asymmetrische Synthese Aufsatzsammlung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=2774561&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016226644&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016226644&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
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