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Acid Catalysis in Modern Organic Synthesis, 2 Volume Set

ISBN: 978-3-527-31724-0
1136 pages
March 2008
Acid Catalysis in Modern Organic Synthesis, 2 Volume Set (3527317244) cover image

Description

This two-volume set covers all new developments and, in addition, includes the hot concept of combined Bronsted and Lewis acid catalysis, developed by Hisashi Yamamoto himself. The excellent editorial team has put together an equally top team of expert authors, resulting in a true treasure trove of essential information -- making this a must for every chemist working in organic chemistry and catalysis, in academia as well as in industry.
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Table of Contents

Preface XIX

List of Contributors XXI

Volume 1

1 Recent Advance of ‘Combined Acid’ Strategy for Asymmetric Catalysis 1
Hisashi Yamamoto and Kentaro Futatsugi

1.1 Combined Acid Catalysis 1

1.2 Super Brønsted Acid Catalyst 29

1.3 Combined Super Brønsted Acid and Lewis Acid System 31

1.4 Conclusion 31

2 Brønsted Acids 35

2.1 Super Brønsted Acid 35
Hisashi Yamamoto, Daisuke Nakashima

2.2 Chiral Brønsted Acids 62
Takahiko Akiyama

3 Li(I), Na(I), and K(I) Lewis Acids 109
Tatsushi Imahori

3.1 Introduction 109

3.2 Alkali Metal Salts as Lewis Acid Reaction Promoter 109

3.3 Lewis Acid Property of Alkali Metals in Organoalkali Metal Reagents 125

3.4 Closing Remarks 130

4 Mg(II), Ca(II), and Zn(II) Lewis Acids 135
Manabu Hatano and Kazuaki Ishihara

4.1 Introduction 135

4.2 Mg(II)-Catalyzed Reactions 136

4.3 Ca(II)-Catalyzed Reactions 149

4.4 Zn(II)-Catalyzed Reactions 151

4.5 Reaction with Mg(II) and Zn(II) Ate Complexes 175

5 Boron (III) Lewis Acids 187
Vivek Rauniyar and Dennis G. Hall

5.1 Introduction 187

5.2 Cycloaddition Reactions 188

5.3 Other Ring-Forming Reactions 196

5.4 Rearrangements and Isomerization Reactions 203

5.5 Nucleophillic Additions to Carbonyl and Imine Compounds 209

5.6 Miscellaneous Reactions 222

5.7 New Types of Boron-Based Lewis Acids 234

5.8 Conclusion 236

6 Al(III) Lewis Acids 241
Takeo Taguchi and Hikaru Yanai

6.1 Introduction 241

6.2 Alkylation 241

6.3 Friedel–Crafts Reactions 245

6.4 Aldol Reactions 250

6.5 Ene Reactions 256

6.6 Carbonyl Additions and Related Reactions 260

6.7 Strained Heterocycles Opening Reactions 279

6.8 Michael Addition Reactions 286

6.9 Cycloaddition Reactions 295

6.10 Claisen Rearrangement 327

6.11 Radical Reactions 331

7 Ga(III) Lewis Acids 347
Ryo Amemiya and Masahiko Yamaguchi

7.1 Introduction 347

7.2 Lewis Acid Activation by Interactions with n Electrons 348

7.3 Lewis Acid Activation by the Interactions with π Electrons 359

7.4 Lewis Acid Activation by Interactions with σ Electrons 367

7.5 Homolysis of Organogallium(III) Compounds 368

7.6 Conclusions 371

8 In(III) Lewis Acids 377
Guan-Leong Chua and Teck-Peng Loh

8.1 Introduction 377

8.2 Aldol and Related Reactions 377

8.3 1,2-Additions to Aldehydes, Ketones and their Synthetic Equivalents 381

8.4 1,4-Addition 391

8.5 Additions to C=N 396

8.6 Ring Opening of Aziridines and Oxiranes 400

8.7 Other Addition Reactions 403

8.8 Electrophilic Aromatic Substitutions 408

8.9 Nucleophilic Substitutions 413

8.10 Cycloaddition Reactions 421

8.11 Prins-type Cyclizations 427

8.12 Other Cyclization Reactions 432

8.13 Oxidations and Reductions 440

8.14 Protection/Deprotection 443

8.15 Miscellaneous Reactions 446

8.16 Asymmetric Catalysis by Chiral Indium Complexes 454

8.17 Conclusion 458

9 Si(IV) Lewis Acids 469
Akira Hosomi and Katsukiyo Miura

9.1 Introduction 469

9.2 Synthetic Use of Silicon Lewis Acids 470

9.3 R3SiX-Promoted Reactions of Acetals and Their Precursors 473

9.4 R3SiX-Promoted Reactions of Carbonyl Compounds 485

9.5 R3SiX-Promoted Reactions of Imines, Aminoacetals, and Related Compounds 496

9.6 R3SiX-Promoted Reactions of Ethers, Esters, Alcohols, and Halides 499

9.7 Other R3SiX-Promoted Reactions 502

9.8 Strained Organosilicon Lewis Acids 503

9.9 Silicon Lewis Acids Activated by Lewis Bases 506

9.10 Concluding Remarks 509

10 Sn(II) and Sn(IV) Lewis Acids 517
Isamu Shiina and Hiroki Fukui

10.1 Introduction 517

10.2 Cycloadditions 517

10.3 Ring-Opening Reactions and Rearrangements 523

10.4 Olefin Activation Reactions 528

10.5 Carbonyl Activation Reactions Including Mukaiyama-Type Reactions 532

10.6 Other Reactions 545

10.7 Conclusions 547

Volume 2

11 Bismuth (III) Lewis Acids 551
Hafida Gaspard-Iloughmane and Christophe Le Roux

11.1 Introduction 551

11.2 Nucleophilic Additions 552

11.3 Cyclization Reactions 560

11.4 Electrophilic Additions 565

11.5 Rearrangements 567

11.6 Ring Opening Reactions 569

11.7 Protection and Deprotection 573

11.8 Oxidation and Reduction Reaction 576

11.9 Miscellaneous Reactions 578

11.10 Green Conditions Involving Bismuth(III) Salts 581

11.11 Conclusion 582

12 Scandium and Yttrium 589
Chikako Ogawa, Yanlong Gu, Marine Boudou and Shu Kobayashi

12.1 Achiral Reactions in Organic Solvent or Solvent-Free Conditions 589

12.2 Asymmetric Reactions in Organic Solvents 606

12.3 Scandium-Catalyzed Reactions in Aqueous Media 620

12.4 Yttrium 625

13 Lanthanide Lewis Acid 635
Masakatsu Shibasaki, Shigeki Matsunaga and Naoya Kumagai

13.1 Introduction 635

13.2 Achiral Lanthanide Lewis Acid Catalysis 636

13.3 Chiral Lanthanide Lewis Acid Catalysis 656

13.4 Lanthanide Bimetallic and Polymetallic Asymmetric Catalysts 670

13.5 Lanthanide–Alkali Metal Heterobimetallic Asymmetric Catalysts 694

13.6 Conclusion 710

14 Titanium Lewis Acid 721
Yu Yuan, Kuiling Ding and Gang Chen

14.1 Introduction 721

14.2 Alkylation, Alkynylation, Vinylation, and Arylation 722

14.3 Allylation 732

14.4 Aldol Reaction 739

14.5 Carbonyl-Ene Reaction 747

14.6 Cycloaddition Reactions 753

14.7 Cyanation 768

14.8 Ring-Opening of Epoxides 777

14.9 Friedel–Crafts Reaction 780

14.10 Baylis–Hillman Reaction 781

14.11 Epoxidation 782

14.12 Sulfoxidation 786

14.13 Halogenation 790

14.14 Reduction 792

14.15 Hydroamination 794

14.16 Miscellaneous 801

14.17 Summary and Outlook 805

15 Zr(IV) and Hf(IV) Lewis Acids 825
Ken-ichiro Kanno and Tamotsu Takahashi

15.1 Introduction 825

15.2 Aldol Reactions 825

15.3 Friedel–Crafts Reactions 834

15.4 Allylations with Allylstannanes 837

15.5 Ring Opening of Three-Membered Cyclic Compounds 839

15.6 Pericyclic Cycloadditions 842

15.7 Carbometalations 846

15.8 Functional Group Transformations 849

16 Transition-Metal Lewis Acids: From Vanadium to Platinum 859
Seiji Iwasa and Hisao Nishiyama

16.1 Introduction 859

16.2 Carbon–Carbon Bond-Forming Reactions 860

16.3 Carbon–Heteroatom Bond-Forming or Cleaving Reactions 891

16.4 Conclusion 897

17 Cu(I) and Cu(II) Lewis Acids 903
Levi M. Stanley and Mukund P. Sibi

17.1 Introduction 903

17.2 Friedel–Crafts Reactions 905

17.3 Claisen Rearrangements 908

17.4 Free-Radical Reactions 909

17.5 Nucleophilic Addition to C=O and C=N Double Bonds 911

17.6 Conjugate Additions 938

17.7 Cycloadditions 943

17.8 Ene Reactions 970

17.9 Nazarov Cyclization 972

17.10 Alkylation, Amination, and Halogenation 973

17.11 Transfer Hydrogenation 976

17.12 Asymmetric Benzoylation 978

17.13 Theoretical Methods 978

17.14 Conclusions 980

18 Ag(I), Au(I), and Au(III) Lewis Acids 987
Akira Yanagisawa

18.1 Introduction 987

18.2 Achiral Silver(I)-Catalyzed Carbon–Carbon Bond Forming Reactions 987

18.3 Chiral Phosphine–Silver(I) Complex-Catalyzed Asymmetric Reactions 992

18.4 Gold(I) and Gold(III)-Catalyzed Carbon–Carbon Bond Forming Reactions 1004

18.5 Summary and Conclusions 1011

19 Polymer-Supported Metal Lewis Acids 1019
Shinichi Itsuno

19.1 Introduction 1019

19.2 Boron-Containing Polymeric Lewis Acid 1020

19.3 Polymer-Supported Aluminum Lewis Acids 1029

19.4 Polymer-Supported Sc Lewis Acids 1035

19.5 Polymer-Supported Ti Lewis Acids 1040

19.6 Polymer-Supported Fe Lewis Acids 1049

19.7 Polymer-Supported Cu Lewis Acids 1050

19.8 Polymer-Supported Zn Lewis Acids 1051

19.9 Polymer-Supported in Lewis Acids 1052

19.10 Polymer-Supported Sn Lewis Acids 1053

19.11 Polymer-Supported Yb Lewis Acids 1054

Index 1061

Reaction Index 1109

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Author Information

Hisashi Yamamoto (born 1943) start his research in Hitosi Nozaki's laboratory at the Kyoto University, Japan. After obtaining his PhD under the mentorship of Elias J. Corey, he joined Toray Industries, Inc., Japan and then he became instructor and then lecturer at Kyoto University. In due course, he was professor at the University of Hawaii and at Nagoya University, Japan. Since 2002 he is Professor at the University of Chicago.
Hisashi Yamamoto's work has been widely acknowledged and honoured with several academic awards and honours (e.g. Max-Tishler Prize, 1998, Le Grand Prix de la Fondation Maison de la Chimie, 2001, Tetrahedron Chair, 2002). He is on editorial boards of several outstanding publications inclusive European Journal of Organic Chemistry and Encyclopedia of Reagents for Organic Synthesis.

Kazuaki Ishihara, born in Nagoya 1963, graduated 1986 at Nagoya University. Thereafter he received 1988 his Master of Engineering, and 1991 Ph.D. Nagoya University (Prof. Hisashi Yamamoto)at the same university. From 1991 to 1992 he was Postdoc at Harvard University (E. J. Corey). He started afterwards his academic career at Nagoya University: 1992-1997 Assistant Professor, 1997-2002 Associate Professor and since 2002 Full Professor.
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Reviews

"Acid Catalysis in Modern Organic Synthesis is an excellent reference book that should be available in every well-equipped chemistry library. It will certainly be helpful for many scientists as a guide through the ever-growing jungle of acids catalysis." (Angewandte Chemie International Edition, January 12, 2009)
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