CATALYSIS MULTICATALYST SYSTEM IN ASYMMETRIC. Wiley. Department of Chemistry

Transcription

1 MULTICATALYST SYSTEM IN ASYMMETRIC CATALYSIS JIAN ZHOU Shanghai Key Laboratory of Green Chemistry and Chemical Processes Department of Chemistry East China Normal University Shanghai, China Wiley

2 Preface Contributors 1 Toward Ideal Asymmetric Catalysis Jian Zhou and Jin-Sheng Yu 1.1 Introduction, Challenges to Realize Ideal Asymmetric Catalysis, Solutions, Borrow Ideas from Nature, Conclusion, 32 References, 32 2 Multicatalyst System Zhong-Yan Cao, Feng Zhu, andjian Zhou 2.1 Introduction, Models of Substrate Activation, The Activation of Electrophiles, The Activation of Nucleophiles, SOMO Catalysis, Early Examples of the Application of Multicatalyst System in Asymmetric Catalysis, A General Introduction of Multicatalyst-Promoted Asymmetric Reactions, 85

3 2.5 Classification of Multicatalyst-Promoted Asymmetric Reactions, Challenges and Possible Solutions, Multicatalyst System Versus Multifunctional Catalyst, Multicatalyst System Versus Additives-Enhanced Catalysis, Additive-Enhanced Catalysis, Nitrogen-containing Organobase, Inorganic Bases, H20, Molecular Sieves and Dehydrators, N-oxide, P-oxide, and As-oxide, Alcohols and Phenols, Ammonium Halides and Metal Halides, Amides, Br0nsted Acids and Lewis Acids, Two or More Additives Together, Conclusion, 147 References, 148 Asymmetric Multifunctional Catalysis 159 Jin-Sheng Yu and Jian Zhou 3.1 Introduction, Asymmetric Multifunctional Organocatalysis, H-Bond Donor-Tertiary Amine Catalysis, H-Bond Donor-Enamine Catalysis, H-Bond Donor-Phase Transfer Catalysis, H-Bond Donor-Tertiary Phosphine Catalysis, Chiral Phosphoric Acid Catalysis, Asymmetric Bifunctional Salt Catalysis, Miscellaneous, Asymmetric Hybrid Organo/Metal Catalysis, Br0nsted Base/Lewis Acid Bifunctional Catalysis, Lewis Base/Lewis Acid Bifunctional Catalysis, Br0nsted Acid/Lewis Acid Bifunctional Catalysis, Enamine/Lewis Acid Bifunctional Catalysis, Hemilable Trisoxazolines, Asymmetric Multifunctional Multimetallic Catalysis, Asymmetric Multifunctional Heteromultimetallic Catalysis, Asymmetric Multifunctional Homomultimetallic Catalysis, Anion-Enabled Bifunctional Asymmetric Catalysis, Ammonium Fluorides or Metal Fluorides, Metal Phosphates, Metal Carboxylates, 265

4 vii Ammonium or Metal Aryloxides, Hydroxides and Alkoxides, Metal Amides, Conclusion, 277 References, Asymmetric Cooperative Catalysis 291 Long Chen, Yun-Lin Liu, and Jian Zhou Introduction, 291 Catalytic Asymmetric Michael Addition Reaction, Combining Multiple Metal Catalysts, Combining Two Distinct Organocatalysts, Combining Metal Catalyst with Organocatalyst, 297 Catalytic Asymmetric Mannich Reaction, Combining Lewis Acid Catalyst and Br0nsted Base Catalyst, Combining Br0nsted Acid Catalyst Catalyst, 301 and Lewis Acid Combining Br0nsted Acid Catalyst and Secondary Amine Catalyst, 303 Catalytic Asymmetric Conia-Ene Reaction, Combining Chiral Lewis Acid and Achiral Lewis Acid, Combining Chiral Br0nsted Base and Achiral Lewis Acid, 306 Catalytic Asymmetric Umpolung Reaction, Combining NHC Catalyst and Lewis Acid Catalyst, Combining NHC Catalyst and Br0nsted Acid Catalyst, 313 Catalytic Asymmetric Cyanosilylation Reaction, 315 cc-alkylation Reaction of Carbonyl Compounds, a-alkylation of Carbonyl Compounds using Alcohols as Alkylation Reagents, a-alkylation of Carbonyl Compounds through Benzylic C-H Bond Oxidation, 325 Catalytic Asymmetric Allylic Alkylation Reaction, Combining Achiral Transition Metal with Chiral LUMO-Lowering Catalysis, Combining Chiral Transition Metal Catalysis with Achiral Organocatalyst, 331 Catalytic Asymmetric Aldol-Type Reaction, 335 Catalytic Asymmetric (Aza)-Morita-Baylis-Hillman Reaction, Chiral Lewis Base/Achiral Acid Cocatalyzed (aza)-mbh Reaction, Achiral Lewis Base/Chiral Acid Cocatalyzed (aza)-mbh Reaction, 342 Catalytic Asymmetric Hydrogenation Reaction, 346

5 viii 4.12 Catalytic Asymmetric Cycloaddition Reaction, [2 + 2] Reaction, [4 + 2] Reaction, Catalytic Asymmetric N H Insertion Reaction, Catalytic Asymmetric a-functionalization of Aldehydes, Miscellaneous Reaction, Conclusion, 364 References, Asymmetric Double Activation Catalysis by Multicatalyst System 373 Long Chen, Zhong-Yan Cao, and Jian Zhou 5.1 Introduction, Double Activation by Aminocatalysis and Lewis Base Catalysis, Asymmetric Double Primary Amine and Br0nsted Acid Catalysis, Diels-Alder (DA)Reaction, Michael Addition, Epoxidation, Miscellaneous Reaction, Asymmetric Double Metal and Br0nsted Base Catalysis, [3 + 2] Cycloaddition, Aldol Reaction, Miscellaneous Reactions, Asymmetric H-Bond Donor Catalysis and Lewis Base Catalysis, Sequential Double Activation Catalysis, Conclusion, 408 References, Asymmetric Assisted Catalysis by Multicatalyst System 411 Xing-Ping Zeng and Jian Zhou 6.1 Introduction, Asymmetric Assisted Catalysis within Acids and Bases, Acid Assisted Acid Catalysis, Base Assisted Br0nsted Acid Catalysis, Lewis Base Assisted Br0nsted Base Catalysis, Acid Assisted Base Catalysis, Miscellaneous, Modulation of a Metal Complex by a Chiral Ligand, Modulation of a Chiral Metal Complex with a Chiral Ligand, Asymmetric Deactivation, Activation, and Deactivation/Activation, Asymmetric Activation of Racemic Catalysts Bearing Tropos Ligand, 460

6 ix 6.4 Supramolecular-Type Assisted Catalysis, Conclusion, 469 References, Asymmetric Catalysis Facilitated by Photochemical or Electrochemical Methods 475 Zhong-Yan Cao and Jian Zhou 7.1 Introduction, Catalytic Asymmetric Reaction Facilitated by Photochemical Method, Asymmetric Oxidation Reactions, a-functionalization of Tertiary Amines, ot-functionalization of Aldehydes, [2 + 2] Photocycloaddition Reaction, Miscellaneous Reactions, Catalytic Asymmetric Reactions Facilitated by Electrochemical Method, Conclusion, 497 References, Multicatalyst System Realized Asymmetric Tandem Reactions 501 Feng Zhou, Yun-Lin Liu, and Jian Zhou 8.1 Introduction, Basic Models of MSRATR, Challenges and Solutions for the Development of MSRATR, Multicatalyst Systems of Homocombination, By Multiple Metal Catalysts, By Multiple Organocatalysts, By Multiple Enzymes, Hetero Combination System Realized MSRATR, By Combination of Metal and Organocatalysts, By Combination of Metal Catalysis and Biocatalysis, By Combination of Organocatalysis and Biocatalysis, Conclusion, 622 References, Waste-Mediated Reactions 633 Jian Zhou and Xing-Ping Zeng 9.1 Introduction, Historical Background, Waste-Promoted Single Reactions, Waste Act as a Br0nsted Base, By-product as Lewis Base, 649

7 X 9.4 By-Products as Acidic Promoter, Waste-Promoted Tandem Reactions, Waste-Catalyzed Tandem Reactions, Conclusions, 666 References, Multicatalyst System Mediated Asymmetric Reactions in Total Synthesis 671 Yun-Lin Liu and Jian Zhou 10.1 Introduction, Application of Multicatalyst System Mediated Single Reactions, Application of Multicatalyst Mediated Tandem Reaction, Conclusion, 685 References, 686 Index 689