Classics in stereoselective synthesis:
"This book provides a noteworthy compilation ofthe groundbreaking methods of stereoselective synthesis, belonging to the repertoire of every modem practitioner of synthetic organic chemistry. The general principles underlying these processes are highlighted as they form the basis for the rapid...
Gespeichert in:
| Hauptverfasser: | , |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2009
|
| Schlagworte: | |
| Online-Zugang: | Inhaltstext Inhaltsverzeichnis |
| Zusammenfassung: | "This book provides a noteworthy compilation ofthe groundbreaking methods of stereoselective synthesis, belonging to the repertoire of every modem practitioner of synthetic organic chemistry. The general principles underlying these processes are highlighted as they form the basis for the rapid and continuing developments in the field. The work also features illustrative examples of drug and natural product syntheses, resulting in a rich source of stimulating ideas for the efficient use of asymmetric reactions in the construction of stereochemically complex structures."--BOOK JACKET. |
| Beschreibung: | XIX, 632 S. Ill., graph. Darst. |
| ISBN: | 9783527299669 9783527324521 |
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Datensatz im Suchindex
| _version_ | 1805091694513750016 |
|---|---|
| adam_text |
Contents
Preface XIII
Acknowledgement XIX
1 Macrocyclic Stereocontrol ]
1.1 Introduction 1
1.2 Background 1
1.3 Conformational Control in Medium-Sized Rings 4
1.4 Asymmetric Synthesis with Medium-Sized Rings 6
1.5 Case Studies in Natural Products Total Synthesis 8
1.6 Macrocyclic Stereocontrol in Cyclic Peptides 14
1.7 Appendix: Macrocycle Formation 14
1.8 Conclusion 15
References 16
2 Carbonyl Addition Reactions 19
2.1 Introduction 19
2.2 Non-Chelated 1,2-Asymmetric Induction and the Operation of
Steric and Electronic Effects 21
2.3 1,2-Asymmetric Induction Predicated on Chelation Control 25
2.4 1,3-Asymmetric Induction from C(3 Stereogenic Centers 29
2.5 Asymmetric Induction by Remote Stereocenters
(Beyond 1,3-Induction) 37
2.6 Catalytic Enantioselective Carbonyl Additions of Organozinc
Species 38
2.7 Enantioselective Ketone Reduction 42
2.8 Enzymatic Reduction of Ketones 49
2.9 Enantioselective Formation of Cyanohydrins 50
2.10 Enantioselective Alkyne Additions 54
2.11 Asymmetric Carbonyl-Ene Reactions 57
2.12 Conclusion 59
References 59
3 a-Functionalizations of Enolates 69
3.1 Introduction 69
3.2 Diastereoselective a-Alkylations of Chiral Enolates 71
3.3 Heteroatom-Substituted Enolates 75
3.4 Asymmetric Enolate Alkylations Using Chiral Auxiliaries 78
3.5 Enantioselective Enolate Alkylations 89
3.6 a-Hydroxylations of Enolates 91
3.7 a-Halogenations of Enolates 94
3.8 Conclusion 96
References 97
Contents
4 Aldol Reactions 103
4.1 Introduction 103
4.2 Chiral Enolates Through the Use of Chiral Auxiliaries
or Chiral Controller Groups 107
4.2.1 Imides 107
4.2.2 Esters 112
4.2.3 Tethered Amides 114
4.2.4 Chiral Boron Reagents 115
4.3 Substrate Control with Chiral Carbonyl Compounds 118
4.4 Catalytic Enantioselective Aldol Reactions 123
4.4.1 Proline-Catalyzed Aldol Additions 123
4.4.2 In Situ Direct Generation of Enolates and Their Asymmetric
Aldol Addition Reactions 124
4.4.3 Enolsilanes and Stannanes 127
4.5 Conclusion 143
References 143
5 Allylations of C=O Bonds 153
5.1 Introduction 153
5.2 Reactivity of Allylmetal Reagents 156
5.3 Boronate Additions 156
5.4 Enantioselective Additions of Optically Active Allylic
Boron Reagents 158
5.5 Diastereoselective Allylations with Chiral Boron Reagents 164
5.6 Mechanistic Aspects - Lewis Acid-Promoted Addition of
Allylsilanes and Allylstannanes to Aldehydes 167
5.7 Chelarion Control in the Allylation of a- and /J-Alkoxy
Aldehydes 168
5.8 Allylchromium Reagents 171
5.9 Diastereoselective Allylations with Chiral Silanes and
Stannanes 172
5.10 Catalytic Asymmetric Allylations 176
5.11 Conclusion 180
References 280
6 Chiral Acetals 187
6.1 Introduction 187
6.2 Diastereoselective Reactions of Chiral Acetals 188
6.3 Glycosylations 198
6.4 Spiroketals in Natural Product Synthesis 204
6.5 Conclusion 208
References 209
7 Alkene Hydroboration 215
7.1 Introduction 235
7.2 Hydroborations with Acyclic Stereocontrol 216
7.3 Metal-Catalyzed Hydroborations 226
7.4 Asymmetric Hydroborations with Chiral Boranes 227
Contents
7.5 Catalytic Asymmetric Hydroboration, Hydrosilylation, and
Hydroalumination 229
7.6 Conclusion 232
References 232
8 Reductions of Olefins 235
8.1 Introduction 235
8.2 Diastereoselective Olefin Reductions by Catalytic
Hydrogenation 236
8.3 Alternative Methods for Diastereoselective Olefin Reductions 243
8.4 Catalytic Asymmetric Olefin Hydrogenations 247
8.5 Conclusion 256
References 256
9 Oxidations of Olefins 263
9.1 Introduction 263
9.2 Diastereoselective Epoxidations 264
9.3 Enantioselective Epoxidations 268
9.4 Asymmetric Ring-Opening of Epoxides 277
9.5 Synthesis of Aziridines 282
9.6 Iodolactonizations and Other Olefin Cydizations Induced
by Electrophiles 285
9.7 Diastereoselective Dihydroxylations of Olefins 291
9.8 Enantioselective Dihydroxylations of Olefins 296
9.9 Enantioselective Aminohydroxylation of Olefins 300
9.10 Conclusion 302
References 303
10 Amino Acids 315
10.1 Introduction 315
10.2 Enantioselective Hydrogenations of a, /3-Didehydroamino
Acids 315
10.3 Enolate Alkylations in the Presence of Chiral Auxiliaries 321
10.4 Alkylation of Glycine Anion Equivalents in the Presence
of Chiral Phase-Transfer Catalysts 324
10.5 Enolate Animations 327
10.6 Enzymatic Syntheses of a-Amino Acids 329
10.7 Catalytic Asymmetric Strecker Reactions 330
10.8 Conclusion 334
References 336
11 Additions to C=N Bonds 343
11.1 Introduction 343
11.2 Substrate-Controlled Diastereoselective Additions to
C=N Bonds 344
11.3 Additions to Imine Derivatives Bearing N-Bound Auxiliaries 349
11.4 Formation of /J-Lactams Through Staudinger Reactions 354
Contents
11.5 Intramolecular Diastereoselective Iminium Ion Cyclizations 356
11.5.1 Diastereoselective Mannich Cyclizations in Complex Molecule
Synthesis 356
11.5.2 Acyliminium Ion and Related Cyclizations 358
11.6 Pictet-Spengler Reactions 359
11.7 Catalytic Asymmetric Reductions of Imines and Imine
Derivatives 362
11.8 Catalytic Enantioselective Mannich and Mannich-Type
Reactions 366
11.9 Enantioselective Additions of Carbon Nucleophiles
to C=N Bonds 370
11.9.1 Enantioselective Allylations of C=N Bonds 370
11.9.2 Catalytic Enantioselective Imino-Ene Reactions 372
11.9.3 Catalytic Enantioselective Additions of Alkylzinc Reagents
to Imines 373
11.9.4 Catalytic Enantioselective Arylations of Imines 375
11.9.5 Catalytic Enantioselective Aza-Henry Reactions 376
11.9.6 Catalytic Enantioselective Cyanations of Ketimines 377
11.10 Conclusion 378
References 379
12 Conjugate Additions 389
12.1 Introduction 3S9
12.2 Diastereoselective Conjugate Additions 390
12.3 Diastereoselective Conjugate Additions with Use of
Chiral Auxiliaries 395
12.4 Enantioselective Conjugate Additions of Enolates and
other Stabilized Carbon Nucleophiles 401
12.5 Enantioselective Conjugate Additions of Organometallic
Species 407
12.6 Enantioselective Conjugate Additions of Radicals 414
12.7 Enantioselective Conjugate Additions of Heteroatom
Nucleophiles 415
12.8 Conjugate Reductions 417
12.9 Catalytic Enantioselective Stetter Reactions 420
12.10 Conclusion 421
References 421
13 Chiral Carbanions 431
13.1 Introduction 431
13.2 Organolithium Reagents by Transmetalation
of Organostannanes 432
13.3 Carbanions by Reductive Methods 434
13.4 Chiral Carbanions by Deprotonation 436
13.5 Sulfoxide- and Phosphorus-Stabilized Carbanions 443
13.6 Metal-Mediated Enantioselective Olefin Functionalizations 446
13.7 Conclusion 451
References 452
Contents
14 Metal-Catalyzed Allylations 457
14.1 Introduction 457
14.2 Diastereoselective Palladium-Catalyzed Allylation Reactions 457
14.3 Enantioselective Palladium-Catalyzed Allylation Reactions 461
14.4 Iridium-Catalyzed Enantioselective Allylation Reactions 466
14.5 Copper-Catalyzed SN2'Allylation Reactions 468
14.6 Enantioselective Allylation Reactions Catalyzed by Other
Transition Metals 471
14.7 Asymmetric Ring-Opening Reactions of Unsaturated
Heterocycles 474
14.8 Conclusion 476
References 477
15 Cyclopropanations and C-H Insertion Reactions 483
15.1 Introduction 483
15.2 Diastereoselective Cyclopropanations with Carbenoids Generated
from Diazoalkanes 485
15.3 Enantioselective Cyclopropanations with Carbenoids Generated
from Diazoalkanes 488
15.4 Diastereoselective Simmons-Smith Cyclopropanations 493
15.5 Enantioselective Simmons-Smith Cyclopropanations 496
15.6 Alternative Classes of Cyclopropanations 497
15.7 Diastereoselective C-H Insertions 501
15.8 Catalytic Enantioselective C-H Insertions 503
15.9 Aminations of C-H Bonds 506
15.10 Conclusion 508
References 509
16 Sigmatropic Rearrangements 515
16.1 Introduction 515
16.2 Claisen and Claisen-Type [3,3]-Sigmatropic Rearrangements 516
16.2.1 Simple Diastereoselectivity in Claisen Rearrangements 518
16.2.2 Diastereoselective Claisen Rearrangements in Complex
Molecule Synthesis 520
16.2.3 Diastereoselective Claisen Rearrangements Using Chiral
Auxiliaries 525
16.2.4 Enantioselective Claisen Rearrangements 526
16.3 Cope and Cope-Type [3,3]-Sigmatropic Rearrangements 528
16.4 [2,3]-Sigmatropic Rearrangements 532
16.4.1 Wittig Rearrangements 534
16.4.2 Sulfoxide, Ammonium, and Oxonium Ylide Rearrangements 536
16.5 Ene Reactions 539
16.6 Nazarov Cydizations 543
16.7 Conclusion 544
References 545
Contents
17 Diels-Alder and Hetero-Diels-Alder Reactions 551
17.1 Introduction 551
17.2 Diastereoselective Intermolecular Diels-Alder Reactions 554
17.3 Diastereoselective Intramolecular Diels-Alder Reactions 556
17.4 Diastereoselective Diels-Alder Reactions Using Chiral
Auxiliaries 560
17.5 Catalytic Enantioselective Diels-Alder Reactions 564
17.6 Diastereoselective Hetero-Diels-Alder Reactions 572
Y7.7 Enantioselective Hetero-Diels-Alder Reactions 576
17.8 Conclusion 580
References 581
18 [3 + 2]-and [2 +2]-Cycloaddition Reactions 589
18.1 Introduction 589
18.2 Substrate-Controlled Diastereoselective [1,3]-Dipolar
Cycloadditions 590
18.3 Diastereoselective [1,3]-Dipolar Cycloadditions Using
Chiral Auxiliaries 596
18.4 Catalytic Enantioselective [1,3]-Dipolar Cycloadditions 599
18.5 [3 + 2]-Cydoadditions with Trimethylenemethane Equivalents 604
18.6 Ketene Cycloadditions 607
18.7 Photochemical [2 + 2]-Cycloadditions 610
18.8 Conclusion 615
References 616
Index 623 |
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| spelling | Carreira, Erick Moran 1963- Verfasser (DE-588)1046866907 aut Classics in stereoselective synthesis Erick M. Carreira and Lisbet Kvaerno Weinheim Wiley-VCH 2009 XIX, 632 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier "This book provides a noteworthy compilation ofthe groundbreaking methods of stereoselective synthesis, belonging to the repertoire of every modem practitioner of synthetic organic chemistry. The general principles underlying these processes are highlighted as they form the basis for the rapid and continuing developments in the field. The work also features illustrative examples of drug and natural product syntheses, resulting in a rich source of stimulating ideas for the efficient use of asymmetric reactions in the construction of stereochemically complex structures."--BOOK JACKET. Asymmetrische Synthese Synthèse asymétrique Asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 s DE-604 Kvaerno, Lisbet Verfasser aut text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3112823&prov=M&dok_var=1&dok_ext=htm Inhaltstext HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017051258&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Carreira, Erick Moran 1963- Kvaerno, Lisbet Classics in stereoselective synthesis Asymmetrische Synthese Synthèse asymétrique Asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd |
| subject_GND | (DE-588)4135603-2 |
| title | Classics in stereoselective synthesis |
| title_auth | Classics in stereoselective synthesis |
| title_exact_search | Classics in stereoselective synthesis |
| title_full | Classics in stereoselective synthesis Erick M. Carreira and Lisbet Kvaerno |
| title_fullStr | Classics in stereoselective synthesis Erick M. Carreira and Lisbet Kvaerno |
| title_full_unstemmed | Classics in stereoselective synthesis Erick M. Carreira and Lisbet Kvaerno |
| title_short | Classics in stereoselective synthesis |
| title_sort | classics in stereoselective synthesis |
| topic | Asymmetrische Synthese Synthèse asymétrique Asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd |
| topic_facet | Asymmetrische Synthese Synthèse asymétrique Asymmetric synthesis |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3112823&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=017051258&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT carreiraerickmoran classicsinstereoselectivesynthesis AT kvaernolisbet classicsinstereoselectivesynthesis |