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Asymmetric Phase Transfer Catalysis
Maruoka, Keiji
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Últimas novedades
química general
química orgánica
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| 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. This title is a must for every synthetic chemist in academia and industry. |
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The Basic Principle of Phase Transfer Catalysis and Some of the Mechanistic Aspects Cinchona-derived Chiral Phase Transfer Catalysts for Amino Acid Synthesis Cinchona-derived Chiral Phase-Transfer Catalysts for Other Asymmetric Synthesis Cinchona-derived Chiral Poly (Phase Transfer Catalysts) for Asymmetric Synthesis Binaphthyl- and Biphenyl-modified Chiral Phase Transfer Catalysts for Asymmetric Synthesis Two-center Chiral Phase Transfer Catalysts for Asymmetric Synthesis Other Chiral Phase Transfer Catalysts for Asymmetric Synthesis Crown Ethers, Taddol, Nobin and Metal(salen) Complexes as Chiral Phase Transfer Catalysts for Asymmetric Synthesis Chiral Quaternary Ammonium Fluorides for Asymmetric Synthesis
Table of Contents
Preface xi
List of Contributors
xiii
The Basic Principle of Phase-Transfer Catalysis and Some Mechanistic Aspects
1 (8)
Takuya Hashimoto
Keiji Maruoka
Introduction
1 (1)
Inorganic Base-Promoted Activation of Acidic Organic Compounds
2 (4)
Generation of Reactive Onium Carbanion Species
2 (1)
Stability of the Onium Carbanion
3 (1)
Reactivity of the Onium Carbanion
3 (1)
Nuclueophilic Substitution Reaction
4 (1)
Nucleophilic Addition to Electrophilic C=X Double Bonds
5 (1)
Phase-Transfer-Catalyzed Addition of Anion Supplied as Metal Salt
6 (1)
Use of Crown Ether as Phase-Transfer Catalyst
7 (2)
References
7 (2)
Cinchona-Derived Chiral Phase-Transfer Catalysts for Amino Acid Synthesis
9 (26)
Takashi Ooi
Introduction
9 (1)
a-Amino Acid Synthesis
9 (20)
Monoalkylation of Schiff Bases Derived from Glycine
9 (10)
Alkylation of Schiff Bases Derived from a-Alkyl-a-Amino Acids
19 (2)
Other Alkylations for a-Amino Acid Synthesis
21 (1)
Michael Reaction of Glycinate Benzophenone Schiff Bases
22 (2)
Aldol and Related Reactions
24 (1)
Aza-Henry Reaction
25 (2)
Strecker Reaction
27 (1)
Aziridination
27 (1)
Radical Reaction
28 (1)
ß-Amino Acid Synthesis
29 (1)
Mannich Reaction
29 (1)
Cyclopropanation
29 (1)
Conclusions
30 (5)
References
31 (4)
Cinchona-Derived Chiral Phase-Transfer Catalysts for Other Asymmetric Synthesis
35 (14)
Shigeru Arai
Introduction
35 (1)
Asymmetric Darzens Reaction
35 (1)
Asymmetric Conjugated Addition
36 (3)
Asymmetric Aldol Reaction
39 (1)
Asymmetric Oxygen-Functionalization
40 (2)
Asymmetric Alkylation
42 (1)
Asymmetric Alkenylation and Alkynylation
43 (2)
Asymmetric SN Aromatic Reaction
45 (1)
Asymmetric Strecker Synthesis
46 (1)
Asymmetric Fluorination
46 (3)
References
47 (2)
Cinchona-Derived Chiral Poly(Phase-Transfer Catalysts) for Asymmetric Synthesis
49 (22)
Sang-sup Jew
Hyeung-geun Park
Cinchona Alkaloids
49 (2)
Cinchona Alkaloids in Asymmetric Phase-Transfer Catalysis
49 (1)
The Origin of Stereoselectivity of Cinchona-PTCs
50 (1)
Development of Dimeric Cinchona-PTCs by the Park--Jew Group
51 (10)
Dimeric Cinchona-PTCs with Phenyl Linker
51 (5)
1,3-Dimeric Cinchona-PTCs with Electronically Modified Phenyl Linker
56 (1)
Polymeric Cinchona-PTCs with Other Linkers
56 (1)
1,3-Phenyl- and 2,7-Naphthyl-Linked Dimeric Cinchona-PTCs
57 (4)
Polymeric PTCs Developed by the Najera Group
61 (1)
Polymeric PTCs Developed by the Siva Group
62 (1)
Polymeric PTCs Developed by the Wang Group
63 (1)
Asymmetric Epoxidation with Polymeric Cinchona-PTCs
63 (5)
Conclusions
68 (3)
References
68 (3)
Binaphthyl- and Biphenyl-Modified Chiral Phase-Transfer Catalysts for Asymmetric Synthesis
71 (44)
Keiji Maruoka
Introduction
71 (1)
Alkylation
71 (28)
Asymmetric Synthesis of a-Alkyl a-Amino Acids and Their Derivatives
71 (1)
Asymmetric Monoalkylation of Glycine Ester Schiff Bases
71 (14)
Asymmetric Monoalkylation of Glycine Amide Schiff Bases
85 (2)
Diastereoselective Alkylation of Glycine Schiff Base with Optically Enriched Alkyl Halides
87 (1)
Recyclable Catalysts and Reagents and Solid-Phase Synthesis
87 (1)
Application of Asymmetric Synthesis of a-Amino Acids
87 (3)
Asymmetric Synthesis of a,a-Dialkyl-a-Amino Acids
90 (4)
Alkylation of Schiff Base-Activated Peptides
94 (3)
Other Alkylations
97 (2)
Michael Addition
99 (6)
Aldol Reaction
105 (1)
Mannich Reaction
106 (1)
Neber Rearrangement
106 (2)
Epoxidation
108 (1)
Strecker Reaction
109 (1)
Conclusions
110 (5)
References
111 (4)
Two-Center Chiral Phase-Transfer Catalysts for Asymmetric Synthesis
115 (20)
Masakatsu Shibasaki
Takashi Ohshima
Introduction
115 (1)
Design and Synthesis of Two-Center Chiral Phase-Transfer Catalyst
115 (3)
Catalytic Asymmetric Phase-Transfer Alkylation
118 (1)
Catalytic Asymmetric Phase-Transfer Michael Addition to a,ß-Unsaturated Esters
119 (1)
Catalytic Asymmetric Phase-Transfer Michael Addition to Enones
120 (2)
Catalytic Asymmetric Phase-Transfer Mannich-Type Reaction
122 (1)
Synthetic Applications
123 (3)
Enantioselective Syntheses of Aeruginosin 298-A and its Analogues
123 (1)
Short Syntheses of (+)-Cylindricine and Formal Synthesis of (--)-Lepadiformine
124 (1)
Formal Synthesis of (+)-CP-99,994 and Total Synthesis of (+)-Nemonapride
125 (1)
Catalyst Recovery and Reuse
126 (1)
Role of Two Ammonium Cations
127 (1)
Other Two-Center Chiral Phase-Transfer Catalysts
128 (4)
Two-Center Chiral Phase-Transfer Catalyst Derived from BINOL (1)
128 (1)
Two-Center Chiral Phase-Transfer Catalyst Derived from BINOL (2)
129 (1)
Two-Center Chiral Phase-Transfer Catalyst Derived from BINOL (3)
129 (1)
Two-Center Chiral Phase-Transfer Catalyst Derived from Tartrate (1)
130 (2)
Two-Center Chiral Phase-Transfer Catalyst Derived from Tartrate (2)
132 (1)
Conclusions
132 (3)
References
133 (2)
Other Chiral Phase-Transfer Catalysts for Asymmetric Synthesis
135 (26)
Hiroaki Sasai
Mahesh L. Patil
Introduction
135 (1)
Other Chiral Phase-Transfer-Catalyzed Reactions
136 (21)
Alkylation
136 (11)
Substrate Scope
147 (2)
Mechanistic Investigations
149 (1)
Michael Reaction
150 (2)
Epoxidation
152 (4)
Hydroxylation
156 (1)
Conclusions
157 (4)
References
157 (4)
Crown Ethers, Taddol, Nobin and Metal(salen) Complexes as Chiral Phase-Transfer Catalysts for Asymmetric Synthesis
161 (28)
Michael North
Introduction
161 (2)
Crown Ethers as Chiral Phase-Transfer Catalysts
163 (3)
Use of Crown Ethers in Asymmetric Michael Additions
163 (2)
Use of Crown Ethers in Darzens Condensations
165 (1)
Use of Crown Ethers in Asymmetric Epoxidations
166 (1)
Use of Taddolates as Chiral Phase-Transfer Catalysts
166 (4)
Use of Nobin and Related Species as Asymmetric Phase-Transfer Catalysts
170 (3)
Use of Metal(salen) Complexes as Chiral Phase-Transfer Catalysts
173 (11)
Nickel(salen) Complexes
173 (2)
Copper(salen) Complexes
175 (7)
Use of Other Metal(salen) Complexes as Catalysts for Enolate Alkylation
182 (1)
Metal(salen) Complexes as Catalysts for Darzens Condensations
183 (1)
Conclusions
184 (5)
References
185 (4)
Chiral Quaternary Ammonium Fluorides for Asymmetric Synthesis
189 (18)
Seiji Shirakawa
Takashi Ooi
Keiji Maruoka
Introduction
189 (1)
In-Situ Generation of Chiral Quaternary Ammonium Fluorides
189 (4)
Chiral Quaternary Ammonium Fluorides: Preparation and Application to Organocatalytic Asymmetric Reactions
193 (4)
Chiral Quaternary Ammonium Bifluorides: Preparation and Use as Organocatalysts for Asymmetric Carbon--Carbon Bond-Forming Reactions
197 (8)
Conclusions
205 (2)
References
205 (2)
Index 207
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