Multicatalyst System in Asymmetric Catalysis E-Book

Jian Zhou

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 1032

Veröffentlichungsjahr: 2014

Beschreibung

This book introduces multi-catalyst systems by describing their mechanism and advantages in asymmetric catalysis. * Helps organic chemists perform more efficient catalysis with step-by-step methods * Overviews new concepts and progress for greener and economic catalytic reactions * Covers topics of interest in asymmetric catalysis including bifunctional catalysis, cooperative catalysis, multimetallic catalysis, and novel tandem reactions * Has applications for pharmaceuticals, agrochemicals, materials, and flavour and fragrance

Leseprobe

Dedicated to my family

MULTICATALYST SYSTEM IN ASYMMETRIC CATALYSIS

JIAN ZHOU

Shanghai Key Laboratory of Green Chemistry and Chemical Processes Department of Chemistry

Copyright © 2015 by John Wiley & Sons, Inc. All rights reserved.

Published by John Wiley & Sons, Inc., Hoboken, New Jersey. Published simultaneously in Canada.

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Library of Congress Cataloging-in-Publication Data:

Multicatalyst system in asymmetric catalysis / Dr. Jian Zhou, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai, China.

pages cm Includes index. ISBN 978-1-118-07186-1 (cloth) 1. Asymmetric synthesis. 2. Catalysis. I. Zhou, Jian, 1974- QD262.Z46 2015 541′.395–dc23

2015017810

CONTENTS

Preface

Contributors

Chapter 1: Toward Ideal Asymmetric Catalysis

1.1 Introduction

1.2 Challenges to Realize Ideal Asymmetric Catalysis

1.3 Solutions

1.4 Borrow ideas from Nature

1.5 Conclusion

References

Chapter 2: Multicatalyst System

2.1 Introduction

2.2 Models of Substrate Activation

2.3 Early Examples of the Application of Multicatalyst System in Asymmetric Catalysis

2.4 A General Introduction of Multicatalyst-Promoted Asymmetric Reactions

2.5 Classification of Multicatalyst-Promoted Asymmetric Reactions

2.6 Challenges and Possible Solutions

2.7 Multicatalyst System Versus Multifunctional Catalyst

2.8 Multicatalyst System Versus Additives-Enhanced Catalysis

2.9 Additive-Enhanced Catalysis

2.10 Conclusion

References

Chapter 3: Asymmetric Multifunctional Catalysis

3.1 Introduction

3.2 Asymmetric Multifunctional Organocatalysis

3.3 Asymmetric Hybrid Organo/Metal Catalysis

3.4 Asymmetric Multifunctional Multimetallic Catalysis

3.5 Anion-Enabled Bifunctional Asymmetric Catalysis

3.6 Conclusion

References

Chapter 4: Asymmetric Cooperative Catalysis

4.1 Introduction

4.2 Catalytic Asymmetric Michael Addition Reaction

4.3 Catalytic Asymmetric Mannich Reaction

4.4 Catalytic Asymmetric Conia-ENE Reaction

4.5 Catalytic Asymmetric Umpolung Reaction

4.6 Catalytic Asymmetric Cyanosilylation Reaction

4.7 α-Alkylation Reaction of Carbonyl Compounds

4.8 Catalytic Asymmetric Allylic Alkylation Reaction

4.9 Catalytic Asymmetric Aldol-Type Reaction

4.10 Catalytic Asymmetric (Aza)-Morita–Baylis–Hillman Reaction

4.11 Catalytic Asymmetric Hydrogenation Reaction

4.12 Catalytic Asymmetric Cycloaddition Reaction

4.13 Catalytic Asymmetric N—H Insertion Reaction

4.14 Catalytic Asymmetric α-Functionalization of Aldehydes

4.15 Miscellaneous Reaction

4.16 Conclusion

References

Chapter 5: Asymmetric Double Activation Catalysis by Multicatalyst System

5.1 Introduction

5.2 Double Activation by Aminocatalysis and Lewis Base Catalysis

5.3 Asymmetric Double Primary Amine and BrØnsted Acid Catalysis

5.4 Asymmetric Double Metal and BrØnsted Base Catalysis

5.5 Asymmetric H-bond Donor Catalysis and Lewis Base Catalysis

5.6 Sequential Double Activation Catalysis

5.7 Conclusion

References

Chapter 6: Asymmetric Assisted Catalysis by Multicatalyst System

6.1 Introduction

6.2 Asymmetric Assisted Catalysis within Acids and Bases

6.3 Modulation of a Metal Complex by a Chiral Ligand

6.4 Supramolecular-Type Assisted Catalysis

6.5 Conclusion

References

Chapter 7: Asymmetric Catalysis Facilitated by Photochemical or Electrochemical Methods

7.1 Introduction

7.2 Catalytic Asymmetric Reaction Facilitated by Photochemical Method

7.3 Catalytic Asymmetric Reactions Facilitated by Electrochemical Method

7.4 Conclusion

References

Chapter 8: Multicatalyst System Realized Asymmetric Tandem Reactions

8.1 Introduction

8.2 Multicatalyst Systems of Homocombination

8.3 Hetero Combination System Realized MSRATR

8.4 Conclusion

References

Note

Chapter 9: Waste-Mediated Reactions

9.1 Introduction

9.2 Historical Background

9.3 Waste-Promoted Single Reactions

9.4 By-Products as Acidic Promoter

9.5 Waste-Promoted Tandem Reactions

9.6 Waste-Catalyzed Tandem Reactions

9.7 Conclusions

References

Chapter 10: Multicatalyst System Mediated Asymmetric Reactions in Total Synthesis

10.1 Introduction

10.2 Application of Multicatalyst System Mediated Single Reactions

10.3 Application of Multicatalyst Mediated Tandem Reaction

10.4 Conclusion

References

Index

End User License Agreement

List of Tables

Chapter 1

Table 1.1

Chapter 2

Table 2.1

Table 2.2

List of Illustrations

Chapter 1

Scheme 1.1 A discussion about the atom utilization of Strecker reaction.

Figure 1.1 Methyl dihydrojasmonate 6 and its presence in some brands of perfumes.

Scheme 1.2 Catalytic asymmetric synthesis of (+)-

cis

-methyl dihydrojasmonate 6.

Figure 1.2 Toward high atom utilization catalytic asymmetric synthesis.

Scheme 1.3 The difference between

N

-Boc protected oxindoles and

N

-methyl analogues.

Scheme 1.4 Definition of ACE and examples of some typical asymmetric reactions.

Scheme 1.5 Evolution of chiral base-catalyzed transamination reaction.

Scheme 1.6 The evolution of catalytic asymmetric aldol reaction.

Scheme 1.7 The evolution of electrophilic amination reaction.

Scheme 1.8 The evolution of asymmetric Diels–Alder reaction.

Scheme 1.9 The evolution of high TON transfer hydrogenation of ketones.

Figure 1.3 Domain organisation of the erythromycin polyketide synthase.

Scheme 1.10 The most concise man-made route to 6-deoxyerythronolide B.

Figure 1.4 The multifunctional H-bonding networks in dihydrofolate reductase.

Figure 1.5 Chorismate mutase enzymes catalyzed Claisen rearrangement.

Figure 1.6 Synergistic catalysis in serine protease enzymes.

Figure 1.7 A hypothetical dual activation model.

Figure 1.8 Proposed catalytic cycle for catechol oxidase activity.

Figure 1.9 The cooperation of a Zn(II) and a Fe(III) for phosphate ester hydrolysis.

Figure 1.10 The cooperation of Cu(II) and Zn(II) in superoxide dismutase.

Figure 1.11 The two types of aldolase mechanisms.

Chapter 2

Figure 2.1 A proposed catalytic cycle involving a single chiral catalyst.

Figure 2.2 Typical processes to furnish central chirality.

Scheme 2.1 Examples to elucidate the formation of chiral center in the transfer step.

Scheme 2.2 Understanding the rate-limiting step of the reaction of 31c and 35d.

Figure 2.3 The concept of monocatalysis.

Figure 2.4 Lewis acid catalysis and some privileged Lewis acids.

Figure 2.5 Secondary interactions in the Lewis acid catalysis.

Scheme 2.3 Transition metal catalysis.

Figure 2.6 H-bond donor catalysis.

Scheme 2.4 Iminium catalysis.

Figure 2.7 Chiral specific Brønsted acid catalysis.

Scheme 2.5 General acid catalysis versus specific acid catalysis.

Figure 2.8 Asymmetric counteranion-directed catalysis.

Scheme 2.6 ACDC catalysis versus iminium catalysis.

Scheme 2.7 Anion-binding catalysis.

Figure 2.9 Brønsted base catalysis.

Figure 2.10 Transition metal catalysis of HOMO-raising activation.

Figure 2.11 Nucleophilic catalysis.

Figure 2.12 Asymmetric enanmine, dienamine, and trienamine catalysis.

Scheme 2.8 The effects of acid cocatalyst on enamine catalysis.

Figure 2.13 Phase-transfer catalysis.

Figure 2.14 Carbene catalysis.

Figure 2.15 SOMO activation strategy.

Scheme 2.9 A dual catalytic system for cyanosilyation of aldehyde.

Scheme 2.10 Combining Rh- and Pd-catalysis for the enantioselective allyl alkylation.

Scheme 2.11 A Lewis acid assisted Brønsted acid catalysis.

Scheme 2.12 Asymmetric aldol reaction of cyclohexanone-derived enol trichloroacetate.

Scheme 2.13 Combined iminium catalysis and Brønsted base catalysis.

Scheme 2.14 Combining chiral PTC with palladium catalysis.

Scheme 2.15 Combining nucleophile/Lewis acid catalysis for synthesizing

β

-lactams.

Scheme 2.16 Asymmetric MBH reaction catalyzed by (

R

)-BINOL derivatives and PEt

3

.

Scheme 2.17 Combining chiral salen derived Lewis acid with an

N

-oxide Lewis base.

Scheme 2.18 Combining chiral Lewis acid catalysis with PTC and Lewis base catalysis.

Scheme 2.19 Combining La and Cu catalysis for allylation of ketones.

Scheme 2.20 Combining Er and Al catalysis for hydrocyanation of olefins.

Scheme 2.21 Cinchona alkaloid-LiClO

4

systems for enantioselective AAC reaction.

Scheme 2.22 Cinchona alkaloid–Lewis acid systems for the asymmetric AAC reaction.

Scheme 2.23 Enantioselective Mannich reaction of α-nitro esters.

Scheme 2.24 Tandem asymmetric Rh catalysis and Pd catalysis.

Scheme 2.25 A tandem hydroformylation/acetalization reaction.

Scheme 2.26 The first dynamic kinetic resolution (DKR) of alcohols by combined rhodium and enzyme catalysis.

Scheme 2.27 The combination of PFL and palladium for the DKR of allylic acetate.

Scheme 2.28 Combination of Rh catalysis with enzyme catalysis for DKR of alcohols.

Scheme 2.29 Combining organocatalysis with enzymatic catalysis.