Asymmetric Phase Transfer Catalysis
Edited by the leading expert on the topic, this is the first book to present the latest developments in this exciting field. Alongside the theoretical aspects, the top contributors provide practical protocols to give readers additional important information otherwise unavailable. A must for every synthetic chemist in academia and industry.
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- Typ dokumentu
- eBook Book
- Jazyk
- English
- Vydáno
-
Newark
Wiley-VCH
2008
John Wiley & Sons, Incorporated - Vydání
- 1. Aufl.
- Témata
- ISBN
- 9783527318421
3527318429 - DOI
- 10.1002/9783527622627
| Abstract | Edited by the leading expert on the topic, this is the first book to present the latest developments in this exciting field. Alongside the theoretical aspects, the top contributors provide practical protocols to give readers additional important information otherwise unavailable. A must for every synthetic chemist in academia and industry. |
|---|---|
| AbstractList | Edited by the leading expert on the topic, this is the first book to present the latest developments in this exciting field. Alongside the theoretical aspects, the top contributors provide practical protocols to give readers additional important information otherwise unavailable. A must for every synthetic chemist in academia and industry. |
| Author | Maruoka, Keiji |
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| SubjectTerms | Asymmetry (Chemistry) Phase-transfer catalysis |
| TableOfContents | 6.5 Catalytic Asymmetric Phase-Transfer Michael Addition to Enones -- 6.6 Catalytic Asymmetric Phase-Transfer Mannich-Type Reaction -- 6.7 Synthetic Applications -- 6.7.1 Enantioselective Syntheses of Aeruginosin 298-A and its Analogues -- 6.7.2 Short Syntheses of (+)-Cylindricine and Formal Synthesis of (-)-Lepadiformine -- 6.7.3 Formal Synthesis of (+)-CP-99,994 and Total Synthesis of (+)-Nemonapride -- 6.8 Catalyst Recovery and Reuse -- 6.9 Role of Two Ammonium Cations -- 6.10 Other Two-Center Chiral Phase-Transfer Catalysts -- 6.10.1 Two-Center Chiral Phase-Transfer Catalyst Derived from BINOL (1) -- 6.10.2 Two-Center Chiral Phase-Transfer Catalyst Derived from BINOL (2) -- 6.10.3 Two-Center Chiral Phase-Transfer Catalyst Derived from BINOL (3) -- 6.10.4 Two-Center Chiral Phase-Transfer Catalyst Derived from Tartrate (1) -- 6.10.5 Two-Center Chiral Phase-Transfer Catalyst Derived from Tartrate (2) -- 6.11 Conclusions -- References -- 7 Other Chiral Phase-Transfer Catalysts for Asymmetric Synthesis -- 7.1 Introduction -- 7.2 Other Chiral Phase-Transfer-Catalyzed Reactions -- 7.2.1 Alkylation -- 7.2.1.1 Substrate Scope -- 7.2.1.2 Mechanistic Investigations -- 7.2.2 Michael Reaction -- 7.2.3 Epoxidation -- 7.2.4 Hydroxylation -- 7.3 Conclusions -- References -- 8 Crown Ethers, Taddol, Nobin and Metal(salen) Complexes as Chiral Phase-Transfer Catalysts for Asymmetric Synthesis -- 8.1 Introduction -- 8.2 Crown Ethers as Chiral Phase-Transfer Catalysts -- 8.2.1 Use of Crown Ethers in Asymmetric Michael Additions -- 8.2.2 Use of Crown Ethers in Darzens Condensations -- 8.2.3 Use of Crown Ethers in Asymmetric Epoxidations -- 8.3 Use of Taddolates as Chiral Phase-Transfer Catalysts -- 8.4 Use of Nobin and Related Species as Asymmetric Phase-Transfer Catalysts -- 8.5 Use of Metal(salen) Complexes as Chiral Phase-Transfer Catalysts Intro -- Asymmetric Phase Transfer Catalysis -- Contents -- Preface -- List of Contributors -- 1 The Basic Principle of Phase-Transfer Catalysis and Some Mechanistic Aspects -- 1.1 Introduction -- 1.2 Inorganic Base-Promoted Activation of Acidic Organic Compounds -- 1.2.1 Generation of Reactive Onium Carbanion Species -- 1.2.2 Stability of the Onium Carbanion -- 1.2.3 Reactivity of the Onium Carbanion -- 1.2.4 Nuclueophilic Substitution Reaction -- 1.2.5 Nucleophilic Addition to Electrophilic C=X Double Bonds -- 1.3 Phase-Transfer-Catalyzed Addition of Anion Supplied as Metal Salt -- 1.4 Use of Crown Ether as Phase-Transfer Catalyst -- References -- 2 Cinchona-Derived Chiral Phase-Transfer Catalysts for Amino Acid Synthesis -- 2.1 Introduction -- 2.2 α-Amino Acid Synthesis -- 2.2.1 Monoalkylation of Schiff Bases Derived from Glycine -- 2.2.2 Alkylation of Schiff Bases Derived from α-Alkyl-α-Amino Acids -- 2.2.3 Other Alkylations for α-Amino Acid Synthesis -- 2.2.4 Michael Reaction of Glycinate Benzophenone Schiff Bases -- 2.2.5 Aldol and Related Reactions -- 2.2.6 Aza-Henry Reaction -- 2.2.7 Strecker Reaction -- 2.2.8 Aziridination -- 2.2.9 Radical Reaction -- 2.3 β-Amino Acid Synthesis -- 2.3.1 Mannich Reaction -- 2.3.2 Cyclopropanation -- 2.4 Conclusions -- References -- 3 Cinchona-Derived Chiral Phase-Transfer Catalysts for Other Asymmetric Synthesis -- 3.1 Introduction -- 3.2 Asymmetric Darzens Reaction -- 3.3 Asymmetric Conjugated Addition -- 3.4 Asymmetric Aldol Reaction -- 3.5 Asymmetric Oxygen-Functionalization -- 3.6 Asymmetric Alkylation -- 3.7 Asymmetric Alkenylation and Alkynylation -- 3.8 Asymmetric S(N) Aromatic Reaction -- 3.9 Asymmetric Strecker Synthesis -- 3.10 Asymmetric Fluorination -- References -- 4 Cinchona-Derived Chiral Poly(Phase-Transfer Catalysts) for Asymmetric Synthesis -- 4.1 Cinchona Alkaloids 4.1.1 Cinchona Alkaloids in Asymmetric Phase-Transfer Catalysis -- 4.1.2 The Origin of Stereoselectivity of Cinchona-PTCs -- 4.2 Development of Dimeric Cinchona-PTCs by the Park-Jew Group -- 4.2.1 Dimeric Cinchona-PTCs with Phenyl Linker -- 4.2.2 1,3-Dimeric Cinchona-PTCs with Electronically Modified Phenyl Linker -- 4.2.3 Polymeric Cinchona-PTCs with Other Linkers -- 4.2.4 1,3-Phenyl- and 2,7-Naphthyl-Linked Dimeric Cinchona-PTCs -- 4.3 Polymeric PTCs Developed by the Najera Group -- 4.4 Polymeric PTCs Developed by the Siva Group -- 4.5 Polymeric PTCs Developed by the Wang Group -- 4.6 Asymmetric Epoxidation with Polymeric Cinchona-PTCs -- 4.7 Conclusions -- References -- 5 Binaphthyl- and Biphenyl-Modified Chiral Phase-Transfer Catalysts for Asymmetric Synthesis -- 5.1 Introduction -- 5.2 Alkylation -- 5.2.1 Asymmetric Synthesis of α-Alkyl α-Amino Acids and Their Derivatives -- 5.2.1.1 Asymmetric Monoalkylation of Glycine Ester Schiff Bases -- 5.2.1.2 Asymmetric Monoalkylation of Glycine Amide Schiff Bases -- 5.2.1.3 Diastereoselective Alkylation of Glycine Schiff Base with Optically Enriched Alkyl Halides -- 5.2.1.4 Recyclable Catalysts and Reagents and Solid-Phase Synthesis -- 5.2.1.5 Application of Asymmetric Synthesis of α-Amino Acids -- 5.2.2 Asymmetric Synthesis of α,α-Dialkyl-α-Amino Acids -- 5.2.3 Alkylation of Schiff Base-Activated Peptides -- 5.2.4 Other Alkylations -- 5.3 Michael Addition -- 5.4 Aldol Reaction -- 5.5 Mannich Reaction -- 5.6 Neber Rearrangement -- 5.7 Epoxidation -- 5.8 Strecker Reaction -- 5.9 Conclusions -- References -- 6 Two-Center Chiral Phase-Transfer Catalysts for Asymmetric Synthesis -- 6.1 Introduction -- 6.2 Design and Synthesis of Two-Center Chiral Phase-Transfer Catalyst -- 6.3 Catalytic Asymmetric Phase-Transfer Alkylation -- 6.4 Catalytic Asymmetric Phase-Transfer Michael Addition to α,β-Unsaturated Esters 8.5.1 Nickel(salen) Complexes -- 8.5.2 Copper(salen) Complexes -- 8.5.3 Use of Other Metal(salen) Complexes as Catalysts for Enolate Alkylation -- 8.5.4 Metal(salen) Complexes as Catalysts for Darzens Condensations -- 8.6 Conclusions -- References -- 9 Chiral Quaternary Ammonium Fluorides for Asymmetric Synthesis -- 9.1 Introduction -- 9.2 In-Situ Generation of Chiral Quaternary Ammonium Fluorides -- 9.3 Chiral Quaternary Ammonium Fluorides: Preparation and Application to Organocatalytic Asymmetric Reactions -- 9.4 Chiral Quaternary Ammonium Bifluorides: Preparation and Use as Organocatalysts for Asymmetric Carbon-Carbon Bond-Forming Reactions -- 9.5 Conclusions -- References -- Index |
| Title | Asymmetric Phase Transfer Catalysis |
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