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Acid catalysis in modern organic synthesis

Author: Hisashi Yamamoto; Kazuaki Ishihara
Publisher: Weinheim : Wiley-VCH ; [Chichester] : [John Wiley, distributor], 2008.
Edition/Format:   Print book : EnglishView all editions and formats
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The sequel to Wiley s bestselling title Lewis Acids in Organic Synthesis, this two-volume set covers all the newest developments in acid catalysis. Crucially, it includes the hot concept of  Read more...

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Additional Physical Format: Online version:
Acid catalysis in modern organic synthesis.
Weinheim : Wiley-VCH ; [Chichester : John Wiley, distributor], 2008
(OCoLC)624474870
Document Type: Book
All Authors / Contributors: Hisashi Yamamoto; Kazuaki Ishihara
ISBN: 9783527317240 3527317244
OCLC Number: 179841449
Description: 2 volumes : illustrations ; 25 cm
Contents: Preface XIX List of Contributors XXI Volume 1 1 Recent Advance of Combined Acid Strategy for Asymmetric Catalysis 1Hisashi Yamamoto and Kentaro Futatsugi 1.1 Combined Acid Catalysis 1 1.2 Super Bronsted Acid Catalyst 29 1.3 Combined Super Bronsted Acid and Lewis Acid System 31 1.4 Conclusion 31 2 Bronsted Acids 35 2.1 Super Bronsted Acid 35Hisashi Yamamoto, Daisuke Nakashima 2.2 Chiral Bronsted Acids 62Takahiko Akiyama 3 Li(I), Na(I), and K(I) Lewis Acids 109Tatsushi 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 135Manabu 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 187Vivek 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 241Takeo 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 347Ryo 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 Electrons 359 7.4 Lewis Acid Activation by Interactions with Electrons 367 7.5 Homolysis of Organogallium(III) Compounds 368 7.6 Conclusions 371 8 In(III) Lewis Acids 377Guan-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 469Akira 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 517Isamu 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 551Hafida 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 589Chikako 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 635Masakatsu 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 721Yu 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 825Ken-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 859Seiji 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 903Levi 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 987Akira 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 1019Shinichi 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
Responsibility: edited by Hisashi Yamamoto and Kazuaki Ishihara.

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