Wiley-VCH - Bücher | Chemie | Asymmetric Organocatalysis

	Bücher \| Chemie \| Asymmetric Organocatalysis \| Inhaltsverzeichnis

Bücher

	Soeben erschienen
	Titelsuche
	Featured Sites

Zeitschriften

	Contents


	Preface	xi
	Foreword	xiii
1	Introduction: Organocatalysis -- From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis	1
	References	8
2	On the Structure of the Book, and a Few General Mechanistic Considerations	9
2.1	The Structure of the Book	9
2.2	General Mechanistic Considerations	9
	References	12
3	Nucleophilic Substitution at Aliphatic Carbon	13
3.1	-Alkylation of Cyclic Ketones and Related Compounds	13
3.2	-Alkylation of -Amino Acid Derivatives	16
3.2.1	Development of Highly Efficient Organocatalysts	16
3.2.2	Improving Enantioselectivity During Work-up	25
3.2.3	Specific Application in the Synthesis of Non-natural Amino Acids	25
3.2.4	Synthesis of ,-Dialkylated Amino Acids	28
3.2.5	Enantio- and Diastereoselective Processes -- Synthesis of -Amino Acid Derivatives with Two Stereogenic Centers	30
3.2.6	Solid-phase Syntheses	31
3.3	-Alkylation of Other Acyclic Substrates	33
3.4	Fluorination, Chlorination, and Bromination Reactions	34
3.4.1	Fluorination Reactions	34
3.4.2	Chlorination and Bromination Reactions	38
	References	41
4	Nucleophilic Addition to Electron-deficient CyC Double Bonds	45
4.1	Intermolecular Michael Addition	45
4.1.1	Intermolecular Michael Addition of C-nucleophiles	47
4.1.1.1	Chiral Bases and Phase-transfer Catalysis	47
4.1.1.2	Activation of Michael Acceptors by Iminium Ion Formation, Activation of Carbonyl Donors by Enamine Formation	55
4.1.1.3	Addition of C-nucleophiles to Azodicarboxylates	69
4.1.1.4	Cyclopropanation of Enoates with Phenacyl Halides	70
4.1.2	Intermolecular Michael Addition of N- and O-nucleophiles	71
4.1.3	Intermolecular Michael Addition of S- and Se-nucleophiles	73
4.2	Intramolecular Michael Addition	78
4.2.1	Intramolecular Michael Addition of C-nucleophiles	78
4.2.2	Intramolecular Michael Addition of O-nucleophiles	79
	References	82
5	Nucleophilic Addition to C=N Double Bonds	85
5.1	Hydrocyanation of Imines (Strecker Reaction)	85
5.1.1	Chiral Diketopiperazines as Catalysts	85
5.1.2	Chiral Guanidines as Catalysts	86
5.1.3	Chiral Ureas and Thioureas as Catalysts	89
5.1.4	Chiral N-Oxides as “Catalysts”	95
5.2	The Mannich Reaction	97
5.2.1	Enantioselective Direct Mannich Reaction: Products with One Stereogenic Center	97
5.2.2	Enantio- and Diastereoselective Direct Mannich Reaction: Products with Two Stereogenic Centers	100
5.2.3	Proline-catalyzed Mannich Reaction: Process Development and Optimization	104
5.2.4	Enantioselective Mannich Reaction using Silyl Ketene Acetals	106
5.3	-Lactam Synthesis	109
5.4	Sulfur Ylide-based Aziridination of Imines	119
5.5	Hydrophosphonylation of Imines	126
	References	126
6	Nucleophilic Addition to C=O Double Bonds	130
6.1	Hydrocyanation	130
6.1.1	The Mechanism of the Reaction	132
6.2	Aldol Reactions	140
6.2.1	Intermolecular Aldol Reactions	140
6.2.1.1	Intermolecular Aldol Reaction With Formation of One Stereogenic Center	140
6.2.1.2	Intermolecular Aldol Reaction with Formation of Two Stereogenic Centers	154
6.2.2	Intramolecular Aldol Reaction	166
6.2.2.1	Intramolecular Aldol Reaction Starting from Diketones	166
6.2.2.2	Intramolecular Aldol Reaction Starting from Triketones	168
6.2.2.3	Intramolecular Aldol Reaction Starting from Dialdehydes	174
6.2.3	Modified Aldol Reactions -- Vinylogous Aldol, Nitroaldol, and Nitrone Aldol Reactions	175
6.3	*-Lactone Synthesis via* Ketene Addition**	179
6.4	The Morita--Baylis--Hillman Reaction	182
6.5	Allylation Reactions	189
6.5.1	Chiral Phosphoramides as Organocatalysts	189
6.5.2	Chiral Formamides as Organocatalysts	197
6.5.3	Chiral Pyridine Derivatives as Organocatalysts	199
6.5.4	Chiral N-Oxides as Organocatalysts	199
6.6	Alkylation of C=O Double Bonds	205
6.7	The Darzens Reaction	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-catalyzed Carbene Formation	219
6.9	The Benzoin Condensation and the Stetter Reaction	227
6.9.1	The Benzoin Condensation	229
6.9.2	The Stetter Reaction	231
6.10	Hydrophosphonylation of C=O Double Bonds	234
	References	236
7	Nucleophilic Addition to Unsaturated Nitrogen	245
7.1	Nucleophilic Addition to N=N Double Bonds	245
7.2	Nucleophilic Addition to N=O Double Bonds	249
	References	254
8	Cycloaddition Reactions	256
8.1	[4+2]-Cycloadditions -- Diels--Alder Reactions	256
8.1.1	Diels--Alder Reactions Using Alkaloids as Organocatalysts	256
8.1.2	Diels--Alder and hetero-Diels--Alder Reactions Using {a}-Amino Acid Derivatives as Organocatalysts	258
8.1.3	Diels--Alder and hetero-Diels--Alder Reactions Using C₂-symmetric Organocatalysts	261
8.2	[3+2]-Cycloadditions: Nitrone- and Electron-deficient Olefin-based Reactions	262
	References	267
9	Protonation of Enolates and Tautomerization of Enols	269
9.1	Enantioselective Protonation of Enolates formed in situ from Enolate Precursors	270
9.2	Enantioselective Tautomerization of Enols Generated in situ	271
9.3	*Enantioselective Protonation of Enolates Generated in situ* from Conjugated Unsaturated Carboxylates**	274
	References	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
10.2.1	Chiral Dioxiranes	290
10.2.2	Peptide Catalysts	290
10.2.3	Phase-transfer Catalysis	299
10.3	Sulfoxidation of Thioethers	303
10.4	Oxidation of Alcohols	306
10.4.1	Kinetic Resolution of Racemic Alcohols	306
10.4.2	Desymmetrization of meso Diols	308
	References	309
11	Reduction of Carbonyl Compounds	314
11.1	Borane Reduction Catalyzed by Oxazaborolidines and Phosphorus-based Catalysts	314
11.2	Borohydride and Hydrosilane Reduction in the Presence of Phase-transfer Catalysts	318
11.3	Reduction with Hydrosilanes in the Presence of Chiral Nucleophilic Activators	319
	References	321
12	Kinetic Resolution of Racemic Alcohols and Amines	323
12.1	Acylation Reactions	323
12.2	Redox Reactions	342
	References	345
13	*Desymmetrization and Kinetic Resolution of Anhydrides; Desymmetrization of meso-Epoxides and other Prochiral Substrates*	347
13.1	Desymmetrization and Kinetic Resolution of Cyclic Anhydrides	347
13.1.1	Desymmetrization of Prochiral Cyclic Anhydrides	349
13.1.2	Kinetic Resolution of Chiral, Racemic Anhydrides	352
13.1.2.1	Kinetic Resolution of 1,3-Dioxolane-2,4-diones (-Hydroxy Acid O-Carboxy Anhydrides)	352
13.1.2.2	Kinetic Resolution of N-Urethane-protected Amino Acid N-Carboxy Anhydrides	355
13.1.3	Parallel Kinetic Resolution of Chiral, Racemic Anhydrides	358
13.1.4	Dynamic Kinetic Resolution of Racemic Anhydrides	358
13.1.4.1	Dynamic Kinetic Resolution of 1,3-Dioxolane-2,4-diones (-Hydroxy acid O-Carboxy Anhydrides)	359
13.1.4.2	Dynamic Kinetic Resolution of N-protected Amino Acid N-Carboxy Anhydrides	360
13.2	Additions to Prochiral Ketenes	363
13.3	*Desymmetrization of meso-Diols*	366
13.3.1	Desymmetrization of meso-Diols by Acylation	367
13.3.2	Desymmetrization of meso-Diols by Oxidation	371
13.4	*Desymmetrization of meso-Epoxides*	374
13.4.1	Enantioselective Isomerization of meso-Epoxides to Allylic Alcohols	374
13.4.2	Enantioselective Ring Opening of meso-Epoxides	381
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

	Bestellen
	Online-Ausgabe
	Inhaltsverzeichnis
	Kurzbeschreibung
	Langtext
	Besprechungen
	Autoreninformation
	Sitz der Autoren


	Amino Acids, Peptides and Proteins in Organic Chemistry 6 Volume Set Catalysis from A to Z A Concise Encyclopedia Organische Chemie Set aus Lehrbuch und Arbeitsbuch
	[mehr >>]


	Angewandte Chemie Angewandte Chemie International Edition Chemie Ingenieur Technik
[mehr>>]


	Krämer, Wolfgang / Schirmer, Ulrich / Jeschke, Peter / Witschel, Matthias (eds.) Modern Crop Protection Compounds 449,- Euro gültig bis 30. Juni 2012
	[mehr Angebote >>]

Seite empfehlen RSS-Feeds Druckversion Sitemap

©2012 Wiley-VCH Verlag GmbH & Co. KGaA - Betreiber
http://www.wiley-vch.de - mailto: info@wiley-vch.de
Datenschutz