Asymmetric organocatalysis: from biomimetic concepts to applications in asymmetric synthesis
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| Main Authors: | , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2005
|
| Edition: | 1. ed., 1. reprint |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XIV, 440 S. Ill. |
| ISBN: | 9783527305179 3527305173 |
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| 100 | 1 | |a Berkessel, Albrecht |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Asymmetric organocatalysis |b from biomimetic concepts to applications in asymmetric synthesis |c Albrecht Berkessel ; Harald Gröger |
| 250 | |a 1. ed., 1. reprint | ||
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2005 | |
| 300 | |a XIV, 440 S. |b Ill. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Catálisis | |
| 650 | 4 | |a Síntesis (Química orgánica) | |
| 650 | 4 | |a Síntesis asimétrica | |
| 650 | 0 | 7 | |a Metallorganische Chemie |0 (DE-588)4602390-2 |2 gnd |9 rswk-swf |
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| 700 | 1 | |a Gröger, Harald |d 1968- |e Verfasser |0 (DE-588)115575561 |4 aut | |
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Record in the Search Index
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|---|---|
| adam_text | ********* ********* * * * * ********* * * * * * * INTRODUCTION :
ORGANOCATALYSIS - FROM B I O M I M E T I C CONCEPTS T O POWERFUL*
M E T H O D S F O R ASYMMETRIE SYNTHESIS 1 * R E F E R E N C E
S 8 * 2 * O N T H E STRUCTURE O F T H E BOOK, AND A
FEW GENERAL M E C H A N I S T I C * CONSIDERATIONS 9 * 2.1* T H E
S T R U C T U R E O F T H E BOOK 9 * 2.2* G E N E R A L
M E C H A N I S T I C C O N S I D E R A T I O N S 9 * R E F
E R E N C E S 12* 3 * N U C L E O P H I L I C S U B S T I T U T
I O N AT ALIPHATIC CARBON 13* 3.1* :X-ALKYLATION O F C Y D I C
K E T O N E S A N D R E L A T E D C O M P O U N D S 13* 3.2*
:X-ALKYLATION O F :X-AMINO ACID D E R I V A T I V E S 16* 3.2.1* D
E V E L O P M E N T O F H I G H L Y E F F I C I E N T O R G
A N O C A T A L Y S T S 16* 3.2.2* I M P R O V I N G E N A N T I O
S E L E C T I V I T Y D U R I N G W O R K - U P 25* 3.2.3* S P
E C I F I C A P P L I C A T I O N I N T H E S Y N T H E S I
S O F N O N - N A T U R A L A M I N O ACIDS 25* 3.2.4* S Y N
T H E S I S O F IX,IX-DIALKYLATED A M I N O ACIDS 28* 3.2.5* E
N A N T I O - A N D D I A S T E R E O S E L E C T I V E P R O C E
S S E S - S Y N T H E S I S O F IX-AMINO* ACID D E R I V A T I
V E S W I T H TWO S T E R E O G E N I C C E N T E R S 30*
3.2.6* S O L I D - P H A S E S Y N T H E S E S 31* 3.3*
IX-ALKYLATION O F O T H E R A C Y D I C S U B S T R A T E S
33* 3.4* F L U O R I N A T I O N , C H L O R I N A T I O N , A N D
B R O M I N A T I O N R E A C T I O N S 34* 3.4.1* F L U O R I
N A T I O N R E A C T I O N S 34* 3.4.2* C H L O R I N A T I O N
A N D B R O M I N A T I O N R E A C T I O N S 38* R E F E R
E N C E S 41* 4 N U D E O P H I L I C ADDITION T O
ELECTRON-DEFICIENT C = C D O U B L E BONDS 45* 4_1 I N T E R M O L
E C U L A R M I C H A E L A D D I T I O N 45* 4.1.1* I N T E R
M O L E C U L A R M I C H A E L A D D I T I O N O F C - N U
D E O P H I L E S 47* 4 . 1 . 1 . 1 * C H I R A L B A S C S
A N D P H A S E - T R A N S F E R C A T A L Y S I S 47*
ASYMMETRIE ORGANOCATALYSIS. A L B R E C H T B E R K E S S E L A N
D H A R A L D G R AE G E R C O P Y R I G H T 2005
W!LEY-VCH V E R L A G G M B H &. CO. K G A A . W E I N H E I M
ISBN: 3-527-30517-3 VI I CONTENTS 4.1.1.2 4.1.1.3 4.1.1.4 4.1.2 4.1.3
4.2 4.2.1 4.2.2 5* 5.1 5.1.1 5.1.2 5.1.3 5.1.4 5.2 5.2.] 5.2.2 5.2.3
5.2.4 5.3 5.4 5.5 6* 6.1 6.1.1 6.2 6.2.1 6.2.1.1 6.2.1.2 6.2.2 6.2.2.1
6.2.2.2 6.2.2.3 6.2.3 6.3 6.4 ACTIVATION OF MICHAEL ACCEPTORS BY IMINIUM
ION FORMATION, ACTIVATION* OF CARBONYJ DONORS BY ENAMINE FORMATION 55*
ADDITION OF C-NUCLEOPHILES TO AZODICARBOXYLATES 69* CYCLOPROPANATION OF
ENOATES WITH PHENACYL HALIDES 70* INTERMOLECULAR MICHAEL ADDITION OF N-
AND O-NUCLEOPHIIES 71* [NTERMOLECULAR MICHAEL ADDITION OF S- AND
SE-NUCLEOPHILES 73* INTRAMOLECULAR MICHAEL ADDITION 78* INTRAMOLECULAR
MICHAEL ADDITION OF C-NUCLEOPHILES 78* INTRAMOLEEULAR MICHAEL ADDITION
OF O-NUCLEOPHILES 79* REFERENCES 82* NUCLEOPHILIC ADDITION TO C=N DOUBLE
BONDS 85* ENANTIOSELECTIVE DIRECT MANNICH REACTION: PRODUCTS WITH ONE*
ENANTIO- AND DIASTEREOSELECTIVE DIRECT MANNICH REACTION: PRODUCTS WITH*
PROLINE-CATALYZED MANNICH REACTION: PROCESS DEVELOPMENT AND*
HYDROCYANATION OF IMINES (STRECKER REACTION) 85* CHIRAL
DIKETOPIPERAZINES AS CATALYSTS 85* CHIRAL GUANIDINES AS CATALYSTS 86*
CHIRAL UREAS AND THIOUREAS AS CATALYSTS 89* CHIRAL N-OXIDES AS
CATALYSTS 95* THE MANNICH REACTION 97* STEREOGENIC CENTER 97* TWO
STEREOGENIC CENTERS 100* OPTIMIZATION 104* ENANTIOSELECTIVE MANNICH
REACTION USING SILYL KETENE ACETALS 106* SS-LACTAM SYNTHESIS 109* SULFUR
YLIDE-BASED AZIRIDINATION OF IMINES 119* HYDROPHOSPHONYLATION OF IMINES
126* REFERENCES 126* NUCLEOPHILIC ADDITION TO C=Q DOUBLE BONDS 130*
INTERMOLEEULAR ALDOL REACTION WITH FORMATION OF ONE STEREOGENIC*
INTERMOLEEULAR ALDOL REACTION WITH FORMATION OF TWO STEREOGENIC*
MODIFIED ALDOL REACTIONS - VINYLOGOUS ALDOL, NITROALDOL, AND NITRONE*
HYDROCYANATION 130* THE MECHANISM OF THE REACTION 132* ALDOL REACTIONS
140* INTERMOLECULAR ALDOL REACTIONS 140* CENTER 140* CENTERS 154*
INTRAMOLECULAR ALDOL REACTION 166* INTRAMOLEEULAR ALDOL REACTION
STARTING FROM DIKETONES 166* INTRAMOLEEULAR ALDOL REACTION STARTING FROM
TRIKETONES 168* INTRAMOLEEULAR ALDOL REACTION STARTING FROM DIALDEHYDES
174* ALDOL REACTIONS 175* SS-LACTONE SYNTHESIS VIA KETENE ADDITION 179*
THE MORITA-BAYLIS-HILLMAN REACTION 182* CONTENTS I VII 6.5* ALLYLATION
REAETIONS 189* 6.5.1* CHIRAL PHOSPHORAMIDES AS ORGANOEATALYSTS 189*
6.5.2* CHIRAL FORMAMIDES AS ORGANOEATALYSTS 197* 6.5.3* CHIRAL PYRIDINE
DERIVATIVES AS ORGANOEATALYSTS 199* 6.5.4* CHIRAL N-OXIDES AS
ORGANOEATALYSTS 199* 6.6* ALKYLATION OF C=O DOUBLE BONDS 205* 6.7* THE
DARZENS REAETION 205* 6.8* SULFUR YLIDE-BASED EPOXIDATION OF ALDEHYDES
211* 6.8.1* EPOXIDE FORMATION FROM YLIDES PREPARED BY MEANS OF BASES
212* 6.8.2* EPOXIDE FORMATION FROM YLIDES PREPARED BY METAL-EATALYZED
CARBENE* FORMATION 219* 6.9* THE BENZOIN CONDENSATION AND THE STEHER
RE~LCTION 227* 6.9.1* THE BENZOIN CONDENSATION 229* 6.9.2* TBE STEHER
REACTION 231* 6.10* HYDROPHOSPHONYLATION OF C=O DOUBLE BONDS 234*
REFERENEES 236* 7* NUCLEOPHILIC ADDITION TO UNSATURATED NITROGEN 245*
7.1* NUCLEOPHILIE ADDITION TO N=N DOUBLE BONDS 245* 7.2* NUCLEOPHILIE
ADDITION TO N=O DOUBLE BONDS 249* REFERENEES 254* 8* CYCLOADDITION
REACTIONS 256* 8.1* [4 + 2]-CYCLOADDITIONS - DIELS-ALDER REAETIONS 2~6
8.1.1* DIELS-ALDER REAETIONS USING ALKALOIDS AS ORGANOEATALYSTS 256*
8.1.2* DIELS-ALDER AND HETERO-DIELS-ALDER RCAETIONS USING (X-AMINO ACID*
DERIVATIVES AS ORGANOEATALYSTS 258* 8.1.3* DIELS-ALDER AND
HETERO-DIELS-ALDER REAETIONS USING C2,SYMMETRIE* ORGANOEATALYSTS 261*
8.2* [3 + 2J-CYC1OADDITIONS: NITRONE* AND ELEETRON-DEFIEIENT
OLEFIN-BASED* REACTIONS 262* REFERENEES 267* 9* PROTONATION OF ENOLATES
AND TAUTOMERIZATION OF ENOLS 269* 9.1* ENANTIOSELEETIVE PROTONATION OF
ENOLATES FORMED IN SITU FROM ENOLATE* PREEURSORS 270* 9.2*
ENANTIOSELEETIVE TAUTOMERIZATION OF ENOLS GENERATED IN SITU 271* 9.3*
ENANTIOSELEETIVE PROTONATION OF FNOLATES GENERATED IN SITU FROM*
CONJUGATED UNSATURATED CARBOXYLATES 274* REFERENEES 275* 10* OXIDATION
277* 10.1* EPOXIDATION OF OLEFINS 277* 10.1.1* CHIRAL DIOXIRANES 277*
10.1.2* CHIRAL IMINIUM IONS 287* 10.2* EPOXIDATION OF ENONES AND ENOATES
290* VIII I CONTENTS 10.2.1 10.2.2 10.2.3 10.3 10.4 10.4.1 10.4.2 11*
11.1 11.2 11.3 12* 12.1 12.2 13* 13.1 13.1.1 13.1.2 13.1.2.1 13.1.2.2
13.1.3 13.1.4 13.1.4.1 13.1.4.2 13.2 13.3 13.3.1 13.3.2 13.4 13.4.1
13.4.2 CHIRAL DIOXIRANCS 290* PEPTIDE CATALYSTS 290* PHASE*TRANSFER
CATALYSIS 299* SULFOXIDATION OF THIOETHERS 303* OXIDATION OF ALCOHOLS
306* KINETIC RESOLUTION OF RACEMIC ALCOHOLS 306* DESYMMETRIZATION OF
MESO DIOLS 308* REFERENCES 309* REDUCTION OF CARBONYL COMPOUNDS 314*
BORANE REDUCTION CATALYZED BY OXAZABOROLIDINES AND PHOSPHORUS-BASED*
BOROHYDRIDE AND HYDROSILANE REDUCTION IN THE PRESENCE OF PHASE-*
REDUCTION WITH HYDROSILANES IN THE PRESENCE OF CHIRAL NUCLEOPHILIC*
CATALYSTS 314* TRANSFER CATALYSTS 318* ACTIVATORS 319* REFERENCES 321*
KINETIC RESOLUTION OF RACEMIC ALCOHOLS AND AMINES 323* ACYLATION
REACTIONS 323* REDOX REACTIONS 342* REFERENCES 345* DESYMMETRIZATION AND
KINETIC RESOLUTION OF ANHYDRIDES; DESYMMETRIZATION* OF MESO-EPOXIDES AND
OTHER PROCHIRAL SUBSTRATES 347* KINETIC RESOLUTION OF
1,3-DIOXOLANE-2,4-DIONES (CT-HYDROXY ACID* KINETIC RESOLUTION OF
N-URETHANE-PROTECTED AMINO ACID N-CARBOXY* DYNAMIC KINETIC RESOLUTION OF
1,3-DIOXOLANE-2,4-DIONES (CI.-HYDROXY ACID* DYNAMIC KINETIC RESOLUTION
OF N-PROTECTED AMINO ACID N-CARBOXY* DESYTMNETRIZATION AND KINETIC
RESOLUTION OF CYCLIC ANHYDRIDES 347* DESYMMETRIZATION OF PROCHIRAL
CYCLIC ANHYDRIDES 349* KINETIC RESOLUTION OF CHIRAL, RACEMIC ANHYDRIDES
352* O-CARBOXY ANHYDRIDES) 352* ANHYDRIDES 355* PARALLEL KINETIC
RESOLUTION OF CHIRAL, RACEMIC ANHYDRIDES 358* DYNAMIC KINETIC RESOLUTION
OF RACEMIC ANHYDRIDES 358* O-CARBOXY ANHYDRIDES) 359* ANHYDRIDES 360*
ADDITIONS TO PROCHIRAL KETENES 363* DESYMMETRIZATION OF MESO-DIOLS 366*
DESYMMETRIZATION OF MESO-DIOLS BY ACYLATION 367* DESYMMETRIZATION OF
MESO-DIOLS BY OXIDATION 371* DESYMMETRIZATION OF MESO-EPOXIDES 374*
ENANTIOSELECTIVE ISOMERIZATION OF MESO-EPOXIDES TO ALLYLIC ALCOHOLS 374*
ENANTIOSELECTIVE RING OPENING OF MESO-FPOXIDES 381* CONTENTS* I IX 13.5*
THE HORNER-WADSWORTH-EMMONS REACTION 383* 13.6* REARRANGEMENT OF O-ACYL
AZLACTONES, O-ACYL OXINDOLES, AND O-ACYL* BENZOFURANONES 385* REFERENCES
389* 14* LARGE-SCALE APPLICATIONS OF ORGANOCATALYSIS 393* 14.1*
INTRODUCTION 393* 14.2* ORGANOCATALYSIS FOR LARGE-SCALE APPLICATIONS:
SOME GENERAL ASPECTS AND* CONSIDERATIONS 393* 14.2.1* ECONOMY OF THE
CATALYST (PRICE/AVAILABILITY) 394* 14.2.2* STABILITY OF THE CATALYSTS
AND HANDLING ISSUES 395* 14.2.3* RECYCLING ISSUES: IMMOBILIZATION OF
ORGANOCATALYSTS 395* 14.2.4* ENANTIOSELECTIVITY, CONVERSION, AND
CATALYTIC LOADING 396* 14.3* LARGE-SCALE ORGANOCATALYTIC REACTION
PROCESSES (SELECTED CASE* STUDIES) 398* 14.3.1* CASE STUDY 1:
JULIA-COLONNA-TYPE EPOXIDATION 398* 14.3.2* CASE STUDY 2: HYDROCYANATION
OF IMINES 401* 14.3.3* CASE STUDY 3: ALKYLATION OF CYCLIC KETONES AND
GLYCINATES 402* 14.3.4* CASE STUDY 4: THE
HAJOS-PARRISH-EDER-WIECHERT-SAUER REACTION 405* REFERENCES 406*
APPENDIX: TABULAR SURVEY OF SELECTED ORGANOCATALYSTS: REACTION SCOPE
AND* AVAILABILITY 409* I* PRIMARY AND SECONDARY AMINE CATALYSTS 410* II*
TERTIARY AMINE AND PYRIDINE CATALYSTS 413* III* PHOSPHANES 417* IV*
PHOSPHORAMIDITES, PHOSPHORAMIDES AND FORMAMIDES 418* V* UREAS,
THIOUREAS, GUANIDINES, AMIDINES 420* VI* KETONES 422* VII* IMINES,
IMINIUM CATIONS AND OXAZOLINES 423* VIII DIOLS 424* IX SULFIDES 425* X*
N-OXIDES AND NITROXYL RADICALS 427* XI* HETEROCYCLIC CARBENES (CARBENE
PRECURSORS) 429* XII* PEPTIDES 430* XIII* PHASE TRANSFER CATALYSTS 433*
INDEX* 436
|
| adam_txt |
********* ********* * * * * ********* * * * * * * INTRODUCTION :
ORGANOCATALYSIS - FROM B I O M I M E T I C CONCEPTS T O POWERFUL*
M E T H O D S F O R ASYMMETRIE SYNTHESIS 1 * R E F E R E N C E
S 8 * 2 * O N T H E STRUCTURE O F T H E BOOK, AND A
FEW GENERAL M E C H A N I S T I C * CONSIDERATIONS 9 * 2.1* T H E
S T R U C T U R E O F T H E BOOK 9 * 2.2* G E N E R A L
M E C H A N I S T I C C O N S I D E R A T I O N S 9 * R E F
E R E N C E S 12* 3 * N U C L E O P H I L I C S U B S T I T U T
I O N AT ALIPHATIC CARBON 13* 3.1* :X-ALKYLATION O F C Y D I C
K E T O N E S A N D R E L A T E D C O M P O U N D S 13* 3.2*
:X-ALKYLATION O F :X-AMINO ACID D E R I V A T I V E S 16* 3.2.1* D
E V E L O P M E N T O F H I G H L Y E F F I C I E N T O R G
A N O C A T A L Y S T S 16* 3.2.2* I M P R O V I N G E N A N T I O
S E L E C T I V I T Y D U R I N G W O R K - U P 25* 3.2.3* S P
E C I F I C A P P L I C A T I O N I N T H E S Y N T H E S I
S O F N O N - N A T U R A L A M I N O ACIDS 25* 3.2.4* S Y N
T H E S I S O F IX,IX-DIALKYLATED A M I N O ACIDS 28* 3.2.5* E
N A N T I O - A N D D I A S T E R E O S E L E C T I V E P R O C E
S S E S - S Y N T H E S I S O F IX-AMINO* ACID D E R I V A T I
V E S W I T H TWO S T E R E O G E N I C C E N T E R S 30*
3.2.6* S O L I D - P H A S E S Y N T H E S E S 31* 3.3*
IX-ALKYLATION O F O T H E R A C Y D I C S U B S T R A T E S
33* 3.4* F L U O R I N A T I O N , C H L O R I N A T I O N , A N D
B R O M I N A T I O N R E A C T I O N S 34* 3.4.1* F L U O R I
N A T I O N R E A C T I O N S 34* 3.4.2* C H L O R I N A T I O N
A N D B R O M I N A T I O N R E A C T I O N S 38* R E F E R
E N C E S 41* 4 N U D E O P H I L I C ADDITION T O
ELECTRON-DEFICIENT C = C D O U B L E BONDS 45* 4_1 I N T E R M O L
E C U L A R M I C H A E L A D D I T I O N 45* 4.1.1* I N T E R
M O L E C U L A R M I C H A E L A D D I T I O N O F C - N U
D E O P H I L E S 47* 4 . 1 . 1 . 1 * C H I R A L B A S C S
A N D P H A S E - T R A N S F E R C A T A L Y S I S 47*
ASYMMETRIE ORGANOCATALYSIS. A L B R E C H T B E R K E S S E L A N
D H A R A L D G R AE G E R C O P Y R I G H T 2005
W!LEY-VCH V E R L A G G M B H &. CO. K G A A . W E I N H E I M
ISBN: 3-527-30517-3 VI I CONTENTS 4.1.1.2 4.1.1.3 4.1.1.4 4.1.2 4.1.3
4.2 4.2.1 4.2.2 5* 5.1 5.1.1 5.1.2 5.1.3 5.1.4 5.2 5.2.] 5.2.2 5.2.3
5.2.4 5.3 5.4 5.5 6* 6.1 6.1.1 6.2 6.2.1 6.2.1.1 6.2.1.2 6.2.2 6.2.2.1
6.2.2.2 6.2.2.3 6.2.3 6.3 6.4 ACTIVATION OF MICHAEL ACCEPTORS BY IMINIUM
ION FORMATION, ACTIVATION* OF CARBONYJ DONORS BY ENAMINE FORMATION 55*
ADDITION OF C-NUCLEOPHILES TO AZODICARBOXYLATES 69* CYCLOPROPANATION OF
ENOATES WITH PHENACYL HALIDES 70* INTERMOLECULAR MICHAEL ADDITION OF N-
AND O-NUCLEOPHIIES 71* [NTERMOLECULAR MICHAEL ADDITION OF S- AND
SE-NUCLEOPHILES 73* INTRAMOLECULAR MICHAEL ADDITION 78* INTRAMOLECULAR
MICHAEL ADDITION OF C-NUCLEOPHILES 78* INTRAMOLEEULAR MICHAEL ADDITION
OF O-NUCLEOPHILES 79* REFERENCES 82* NUCLEOPHILIC ADDITION TO C=N DOUBLE
BONDS 85* ENANTIOSELECTIVE DIRECT MANNICH REACTION: PRODUCTS WITH ONE*
ENANTIO- AND DIASTEREOSELECTIVE DIRECT MANNICH REACTION: PRODUCTS WITH*
PROLINE-CATALYZED MANNICH REACTION: PROCESS DEVELOPMENT AND*
HYDROCYANATION OF IMINES (STRECKER REACTION) 85* CHIRAL
DIKETOPIPERAZINES AS CATALYSTS 85* CHIRAL GUANIDINES AS CATALYSTS 86*
CHIRAL UREAS AND THIOUREAS AS CATALYSTS 89* CHIRAL N-OXIDES AS
"CATALYSTS" 95* THE MANNICH REACTION 97* STEREOGENIC CENTER 97* TWO
STEREOGENIC CENTERS 100* OPTIMIZATION 104* ENANTIOSELECTIVE MANNICH
REACTION USING SILYL KETENE ACETALS 106* SS-LACTAM SYNTHESIS 109* SULFUR
YLIDE-BASED AZIRIDINATION OF IMINES 119* HYDROPHOSPHONYLATION OF IMINES
126* REFERENCES 126* NUCLEOPHILIC ADDITION TO C=Q DOUBLE BONDS 130*
INTERMOLEEULAR ALDOL REACTION WITH FORMATION OF ONE STEREOGENIC*
INTERMOLEEULAR ALDOL REACTION WITH FORMATION OF TWO STEREOGENIC*
MODIFIED ALDOL REACTIONS - VINYLOGOUS ALDOL, NITROALDOL, AND NITRONE*
HYDROCYANATION 130* THE MECHANISM OF THE REACTION 132* ALDOL REACTIONS
140* INTERMOLECULAR ALDOL REACTIONS 140* CENTER 140* CENTERS 154*
INTRAMOLECULAR ALDOL REACTION 166* INTRAMOLEEULAR ALDOL REACTION
STARTING FROM DIKETONES 166* INTRAMOLEEULAR ALDOL REACTION STARTING FROM
TRIKETONES 168* INTRAMOLEEULAR ALDOL REACTION STARTING FROM DIALDEHYDES
174* ALDOL REACTIONS 175* SS-LACTONE SYNTHESIS VIA KETENE ADDITION 179*
THE MORITA-BAYLIS-HILLMAN REACTION 182* CONTENTS I VII 6.5* ALLYLATION
REAETIONS 189* 6.5.1* CHIRAL PHOSPHORAMIDES AS ORGANOEATALYSTS 189*
6.5.2* CHIRAL FORMAMIDES AS ORGANOEATALYSTS 197* 6.5.3* CHIRAL PYRIDINE
DERIVATIVES AS ORGANOEATALYSTS 199* 6.5.4* CHIRAL N-OXIDES AS
ORGANOEATALYSTS 199* 6.6* ALKYLATION OF C=O DOUBLE BONDS 205* 6.7* THE
DARZENS REAETION 205* 6.8* SULFUR YLIDE-BASED EPOXIDATION OF ALDEHYDES
211* 6.8.1* EPOXIDE FORMATION FROM YLIDES PREPARED BY MEANS OF BASES
212* 6.8.2* EPOXIDE FORMATION FROM YLIDES PREPARED BY METAL-EATALYZED
CARBENE* FORMATION 219* 6.9* THE BENZOIN CONDENSATION AND THE STEHER
RE~LCTION 227* 6.9.1* THE BENZOIN CONDENSATION 229* 6.9.2* TBE STEHER
REACTION 231* 6.10* HYDROPHOSPHONYLATION OF C=O DOUBLE BONDS 234*
REFERENEES 236* 7* NUCLEOPHILIC ADDITION TO UNSATURATED NITROGEN 245*
7.1* NUCLEOPHILIE ADDITION TO N=N DOUBLE BONDS 245* 7.2* NUCLEOPHILIE
ADDITION TO N=O DOUBLE BONDS 249* REFERENEES 254* 8* CYCLOADDITION
REACTIONS 256* 8.1* [4 + 2]-CYCLOADDITIONS - DIELS-ALDER REAETIONS 2~6
8.1.1* DIELS-ALDER REAETIONS USING ALKALOIDS AS ORGANOEATALYSTS 256*
8.1.2* DIELS-ALDER AND HETERO-DIELS-ALDER RCAETIONS USING (X-AMINO ACID*
DERIVATIVES AS ORGANOEATALYSTS 258* 8.1.3* DIELS-ALDER AND
HETERO-DIELS-ALDER REAETIONS USING C2,SYMMETRIE* ORGANOEATALYSTS 261*
8.2* [3 + 2J-CYC1OADDITIONS: NITRONE* AND ELEETRON-DEFIEIENT
OLEFIN-BASED* REACTIONS 262* REFERENEES 267* 9* PROTONATION OF ENOLATES
AND TAUTOMERIZATION OF ENOLS 269* 9.1* ENANTIOSELEETIVE PROTONATION OF
ENOLATES FORMED IN SITU FROM ENOLATE* PREEURSORS 270* 9.2*
ENANTIOSELEETIVE TAUTOMERIZATION OF ENOLS GENERATED IN SITU 271* 9.3*
ENANTIOSELEETIVE PROTONATION OF FNOLATES GENERATED IN SITU FROM*
CONJUGATED UNSATURATED CARBOXYLATES 274* REFERENEES 275* 10* OXIDATION
277* 10.1* EPOXIDATION OF OLEFINS 277* 10.1.1* CHIRAL DIOXIRANES 277*
10.1.2* CHIRAL IMINIUM IONS 287* 10.2* EPOXIDATION OF ENONES AND ENOATES
290* VIII I CONTENTS 10.2.1 10.2.2 10.2.3 10.3 10.4 10.4.1 10.4.2 11*
11.1 11.2 11.3 12* 12.1 12.2 13* 13.1 13.1.1 13.1.2 13.1.2.1 13.1.2.2
13.1.3 13.1.4 13.1.4.1 13.1.4.2 13.2 13.3 13.3.1 13.3.2 13.4 13.4.1
13.4.2 CHIRAL DIOXIRANCS 290* PEPTIDE CATALYSTS 290* PHASE*TRANSFER
CATALYSIS 299* SULFOXIDATION OF THIOETHERS 303* OXIDATION OF ALCOHOLS
306* KINETIC RESOLUTION OF RACEMIC ALCOHOLS 306* DESYMMETRIZATION OF
MESO DIOLS 308* REFERENCES 309* REDUCTION OF CARBONYL COMPOUNDS 314*
BORANE REDUCTION CATALYZED BY OXAZABOROLIDINES AND PHOSPHORUS-BASED*
BOROHYDRIDE AND HYDROSILANE REDUCTION IN THE PRESENCE OF PHASE-*
REDUCTION WITH HYDROSILANES IN THE PRESENCE OF CHIRAL NUCLEOPHILIC*
CATALYSTS 314* TRANSFER CATALYSTS 318* ACTIVATORS 319* REFERENCES 321*
KINETIC RESOLUTION OF RACEMIC ALCOHOLS AND AMINES 323* ACYLATION
REACTIONS 323* REDOX REACTIONS 342* REFERENCES 345* DESYMMETRIZATION AND
KINETIC RESOLUTION OF ANHYDRIDES; DESYMMETRIZATION* OF MESO-EPOXIDES AND
OTHER PROCHIRAL SUBSTRATES 347* KINETIC RESOLUTION OF
1,3-DIOXOLANE-2,4-DIONES (CT-HYDROXY ACID* KINETIC RESOLUTION OF
N-URETHANE-PROTECTED AMINO ACID N-CARBOXY* DYNAMIC KINETIC RESOLUTION OF
1,3-DIOXOLANE-2,4-DIONES (CI.-HYDROXY ACID* DYNAMIC KINETIC RESOLUTION
OF N-PROTECTED AMINO ACID N-CARBOXY* DESYTMNETRIZATION AND KINETIC
RESOLUTION OF CYCLIC ANHYDRIDES 347* DESYMMETRIZATION OF PROCHIRAL
CYCLIC ANHYDRIDES 349* KINETIC RESOLUTION OF CHIRAL, RACEMIC ANHYDRIDES
352* O-CARBOXY ANHYDRIDES) 352* ANHYDRIDES 355* PARALLEL KINETIC
RESOLUTION OF CHIRAL, RACEMIC ANHYDRIDES 358* DYNAMIC KINETIC RESOLUTION
OF RACEMIC ANHYDRIDES 358* O-CARBOXY ANHYDRIDES) 359* ANHYDRIDES 360*
ADDITIONS TO PROCHIRAL KETENES 363* DESYMMETRIZATION OF MESO-DIOLS 366*
DESYMMETRIZATION OF MESO-DIOLS BY ACYLATION 367* DESYMMETRIZATION OF
MESO-DIOLS BY OXIDATION 371* DESYMMETRIZATION OF MESO-EPOXIDES 374*
ENANTIOSELECTIVE ISOMERIZATION OF MESO-EPOXIDES TO ALLYLIC ALCOHOLS 374*
ENANTIOSELECTIVE RING OPENING OF MESO-FPOXIDES 381* CONTENTS* I IX 13.5*
THE HORNER-WADSWORTH-EMMONS REACTION 383* 13.6* REARRANGEMENT OF O-ACYL
AZLACTONES, O-ACYL OXINDOLES, AND O-ACYL* BENZOFURANONES 385* REFERENCES
389* 14* LARGE-SCALE APPLICATIONS OF ORGANOCATALYSIS 393* 14.1*
INTRODUCTION 393* 14.2* ORGANOCATALYSIS FOR LARGE-SCALE APPLICATIONS:
SOME GENERAL ASPECTS AND* CONSIDERATIONS 393* 14.2.1* ECONOMY OF THE
CATALYST (PRICE/AVAILABILITY) 394* 14.2.2* STABILITY OF THE CATALYSTS
AND HANDLING ISSUES 395* 14.2.3* RECYCLING ISSUES: IMMOBILIZATION OF
ORGANOCATALYSTS 395* 14.2.4* ENANTIOSELECTIVITY, CONVERSION, AND
CATALYTIC LOADING 396* 14.3* LARGE-SCALE ORGANOCATALYTIC REACTION
PROCESSES (SELECTED CASE* STUDIES) 398* 14.3.1* CASE STUDY 1:
JULIA-COLONNA-TYPE EPOXIDATION 398* 14.3.2* CASE STUDY 2: HYDROCYANATION
OF IMINES 401* 14.3.3* CASE STUDY 3: ALKYLATION OF CYCLIC KETONES AND
GLYCINATES 402* 14.3.4* CASE STUDY 4: THE
HAJOS-PARRISH-EDER-WIECHERT-SAUER REACTION 405* REFERENCES 406*
APPENDIX: TABULAR SURVEY OF SELECTED ORGANOCATALYSTS: REACTION SCOPE
AND* AVAILABILITY 409* I* PRIMARY AND SECONDARY AMINE CATALYSTS 410* II*
TERTIARY AMINE AND PYRIDINE CATALYSTS 413* III* PHOSPHANES 417* IV*
PHOSPHORAMIDITES, PHOSPHORAMIDES AND FORMAMIDES 418* V* UREAS,
THIOUREAS, GUANIDINES, AMIDINES 420* VI* KETONES 422* VII* IMINES,
IMINIUM CATIONS AND OXAZOLINES 423* VIII DIOLS 424* IX SULFIDES 425* X*
N-OXIDES AND NITROXYL RADICALS 427* XI* HETEROCYCLIC CARBENES (CARBENE
PRECURSORS) 429* XII* PEPTIDES 430* XIII* PHASE TRANSFER CATALYSTS 433*
INDEX* 436 |
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| author | Berkessel, Albrecht Gröger, Harald 1968- |
| author_GND | (DE-588)115575561 |
| author_facet | Berkessel, Albrecht Gröger, Harald 1968- |
| author_role | aut aut |
| author_sort | Berkessel, Albrecht |
| author_variant | a b ab h g hg |
| building | Verbundindex |
| bvnumber | BV021675678 |
| classification_rvk | VK 5500 |
| classification_tum | CHE 622f CHE 624f CHE 330f |
| ctrlnum | (OCoLC)318364150 (DE-599)BVBBV021675678 |
| 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 Chemie |
| discipline_str_mv | Chemie / Pharmazie Chemie |
| edition | 1. ed., 1. reprint |
| format | Book |
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| id | DE-604.BV021675678 |
| illustrated | Illustrated |
| index_date | 2024-07-02T15:09:59Z |
| indexdate | 2024-07-09T20:41:23Z |
| institution | BVB |
| isbn | 9783527305179 3527305173 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-014889968 |
| oclc_num | 318364150 |
| open_access_boolean | |
| owner | DE-29T DE-83 |
| owner_facet | DE-29T DE-83 |
| physical | XIV, 440 S. Ill. |
| publishDate | 2005 |
| publishDateSearch | 2005 |
| publishDateSort | 2005 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Berkessel, Albrecht Verfasser aut Asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis Albrecht Berkessel ; Harald Gröger 1. ed., 1. reprint Weinheim Wiley-VCH 2005 XIV, 440 S. Ill. txt rdacontent n rdamedia nc rdacarrier Catálisis Síntesis (Química orgánica) Síntesis asimétrica Metallorganische Chemie (DE-588)4602390-2 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Katalyse (DE-588)4029921-1 gnd rswk-swf Metallorganische Chemie (DE-588)4602390-2 s Asymmetrische Synthese (DE-588)4135603-2 s Katalyse (DE-588)4029921-1 s b DE-604 Gröger, Harald 1968- Verfasser (DE-588)115575561 aut OEBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014889968&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Berkessel, Albrecht Gröger, Harald 1968- Asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis Catálisis Síntesis (Química orgánica) Síntesis asimétrica Metallorganische Chemie (DE-588)4602390-2 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Katalyse (DE-588)4029921-1 gnd |
| subject_GND | (DE-588)4602390-2 (DE-588)4135603-2 (DE-588)4029921-1 |
| title | Asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis |
| title_auth | Asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis |
| title_exact_search | Asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis |
| title_exact_search_txtP | Asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis |
| title_full | Asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis Albrecht Berkessel ; Harald Gröger |
| title_fullStr | Asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis Albrecht Berkessel ; Harald Gröger |
| title_full_unstemmed | Asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis Albrecht Berkessel ; Harald Gröger |
| title_short | Asymmetric organocatalysis |
| title_sort | asymmetric organocatalysis from biomimetic concepts to applications in asymmetric synthesis |
| title_sub | from biomimetic concepts to applications in asymmetric synthesis |
| topic | Catálisis Síntesis (Química orgánica) Síntesis asimétrica Metallorganische Chemie (DE-588)4602390-2 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Katalyse (DE-588)4029921-1 gnd |
| topic_facet | Catálisis Síntesis (Química orgánica) Síntesis asimétrica Metallorganische Chemie Asymmetrische Synthese Katalyse |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014889968&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT berkesselalbrecht asymmetricorganocatalysisfrombiomimeticconceptstoapplicationsinasymmetricsynthesis AT grogerharald asymmetricorganocatalysisfrombiomimeticconceptstoapplicationsinasymmetricsynthesis |