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E-raamat: Enantioselection in Asymmetric Catalysis

Pavel A. Dub, Ilya D. Gridnev (Tohoku University, Sendai, Japan)

Formaat: EPUB+DRM
Ilmumisaeg: 03-Nov-2016
Kirjastus: CRC Press Inc
Keel: eng
ISBN-13: 9781315353340

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Formaat: EPUB+DRM
Ilmumisaeg: 03-Nov-2016
Kirjastus: CRC Press Inc
Keel: eng
ISBN-13: 9781315353340

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The field of asymmetric catalysis is currently one of the hottest areas in chemistry. This unique book focuses on the mechanism of enantioselectivity in asymmetric catalysis, rather than asymmetric catalysis from the synthetic view. It describes reliable, experimentally and computationally supported mechanisms, and discusses the danger of so-called "plausible" or "accepted" mechanisms leading to wrong conclusions. It draws parallels to enzymatic catalysis in biochemistry, and examines in detail the physico-chemical aspects of enantioselective catalysis.

Introduction

Authors

Chapter 1 Transition metal-catalyzed hydrogenation

(132)

1.1 Rh-catalyzed asymmetric hydrogenation of activated olefins

(67)

1.1.1 Overview

(1)

1.1.2 Asymmetric hydrogenation catalyzed by Rh--diphosphine ligands

(1)

1.1.2.1 Resting state of the catalytic cycle: Formation of the catalyst--substrate complexes

(7)

1.1.2.2 Activation of H2

(4)

1.1.2.3 Formation of solvate dihydrides

(3)

1.1.2.4 Oxidative addition to chelate catalyst--substrate complexes

(7)

1.1.2.5 Reactions of solvate dihydrides with prochiral substrates

(11)

1.1.2.6 Catalytic cycle and enantioselective step

(4)

1.1.2.7 Process of enantioselection

(17)

1.1.2.8 Sense of enantioselection and the relative size of substituents

(8)

1.1.3 Catalysis with rhodium complexes of monophosphines

(3)

1.1.4 Conclusions

(3)

1.2 Ru-catalyzed asymmetric hydrogenation and transfer hydrogenation of ketones

(26)

1.2.1 Overview

(3)

1.2.2 A Brief Critical Overview of Experimental and Computational Techniques Used in the Early Mechanistic Studies of 1 and 2

(1)

1.2.2.1 The characteristic time and sensitivity of NMR spectroscopy

(1)

1.2.2.2 Kinetics

(2)

1.2.2.3 Computations in the gas-phase

(1)

1.2.3 Progress of the reaction mechanism with 1 and 2

(11)

1.2.4 The origin of the enantioselectivity

(4)

1.2.5 Unresolved problems

(1)

1.2.5.1 Reaction mechanism

(3)

1.2.5.2 Enantioselectivity

(2)

1.3 Ir-catalyzed asymmetric hydrogenation of C=C and C=N bonds

(10)

1.3.1 Overview

(1)

1.3.2 Catalytic cycle and intermediates

(3)

1.3.3 Mechanism of enantioselection

(1)

1.3.3.1 Simple olefins

(2)

1.3.3.2 Imines

100

(1)

1.3.3.3 Heterocycles

101

(3)

1.3.4 Conclusion

104

(1)

1.4 Pd-catalyzed asymmetric hydrogenation of indoles

104

(29)

1.4.1 Overview

104

(1)

1.4.2 Catalytic cycle

105

(1)

1.4.3 Enantioselectivity

106

(2)

References

108

(25)

Chapter 2 Other enantioselective reactions catalyzed by transition metals

133

(50)

2.1 Enantioselective reactions catalyzed by bifunctional Ru and Ir complexes

133

(10)

2.1.1 Mechanism of the Michael addition catalyzed by bifunctional Ru catalysts

133

(2)

2.1.2 Mechanism of C--C and C--N bond forming reactions catalyzed by bifunctional Ir catalysts

135

(8)

2.2 Rh-catalyzed stereoselective isomerization of tert-cyclobutanols into chiral indanoles

143

(4)

2.2.1 Overview

143

(1)

2.2.2 Catalytic cycle

144

(3)

2.3 Os-catalyzed asymmetric dihydroxylation (Sharpless reaction)

147

(5)

2.3.1 Overview

147

(2)

2.3.2 Catalytic cycle

149

(1)

2.3.3 Enantioselectivity

149

(3)

2.4 Pd- and Rh-catalyzed conjugate additions of arylboronic acids to enones and nitrostyrenes (Hayashi--Miyaura reaction)

152

(6)

2.4.1 Overview

152

(1)

2.4.2 Catalytic cycle

152

(2)

2.4.3 Catalytic cycle (M = Rh, Scheme 2.12)

154

(1)

2.4.4 Origin of enantioselectivity (M = Pd)

155

(2)

2.4.5 Origin of enantioselectivity (M = Rh)

157

(1)

2.5 Rh-catalyzed asymmetric hydroboration of vinylarenes

158

(6)

2.5.1 Overview

158

(2)

2.5.2 Catalytic cycle

160

(1)

2.5.3 Enantioselectivity

161

(3)

2.6 Mechanism of autoamplifying Soai reaction

164

(19)

2.6.1 Introduction

164

(2)

2.6.2 Studies of the reaction pool of Soai reaction

166

(2)

2.6.3 Structure of the catalyst and computations of the catalytic cycle of Soai reaction

168

(4)

References

172

(11)

Chapter 3 Mechanism of enantioselection in organocatalytic reactions

183

(42)

3.1 Phosphoric acids

183

(9)

3.1.1 Asymmetric allylboration

183

(1)

3.1.2 Kinetic resolution in Robinson-type cyclization

184

(1)

3.1.3 Friedel--Crafts alkylation of indoles with nitroalkenes

185

(3)

3.1.4 Petasis--Ferrier-type rearrangement

188

(2)

3.1.5 Enantioselective indole aza-Claisen rearrangement

190

(1)

3.1.6 Asymmetric thiocarboxylysis of meso-epoxide

190

(2)

3.1.7 Asymmetric sulfoxidation reaction

192

(1)

3.2 Cinchona alkaloids

192

(9)

3.2.1 Asymmetric olefin isomerization

194

(1)

3.2.2 Friedel--Crafts alkylation of indoles with α, β-unsaturated ketones

195

(3)

3.2.3 Conjugate addition of dimethyl malonate to β-nitrostyrene

198

(1)

3.2.4 Fluorination of cyclic ketones

199

(1)

3.2.5 Phase-transfer-catalyzed alkylation reaction

200

(1)

3.3 Urea and thiourea-based catalysts

201

(11)

3.3.1 Catalytic Strecker reaction

202

(1)

3.3.2 Michael addition reactions

203

(2)

3.3.3 Enantioselective decarboxylative protonation

205

(2)

3.3.4 Henry reaction

207

(2)

3.3.5 α-Hydroxylation of β-ketoesters

209

(3)

3.4 N-Protonated chiral oxazaborolidine

212

(2)

3.4.1 C--C insertion reaction

212

(2)

3.5 FLP-catalyzed asymmetric hydrogenation of imines and enamines

214

(11)

3.5.1 Overview

214

(2)

3.5.2 Catalytic cycle

216

(1)

3.5.3 Enantioselectivity

216

(2)

References

218

(7)

Conclusions

225

(4)

Index

229

Ilya Gridnev is an associate professor at Tohoku University, Sendai, Japan. Pavel A. Dub is a J. Robert Oppenheimer postdoctoral fellow at Los Alamos National Laboratory, New Mexico, USA.

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