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Organocatalytic Enantioselective Conjugate Addition Reactions : A Powerful Tool for the Stereocontrolled Synthesis of Complex Molecules.
Title:
Organocatalytic Enantioselective Conjugate Addition Reactions : A Powerful Tool for the Stereocontrolled Synthesis of Complex Molecules.
Author:
Vicario, Jose L.
ISBN:
9781849732185
Personal Author:
Edition:
1st ed.
Physical Description:
1 online resource (365 pages)
Series:
Catalysis Series ; v.5

Catalysis Series
Contents:
Organocatalytic Enantioselective Conjugate Addition Reactions -- Contents -- Chapter 1 Introduction -- 1.1 Organocatalysis: an Emerging Field -- 1.2 Historical Evolution of Asymmetric Organocatalysis -- 1.3 Types of Organocatalysts -- 1.4 The Conjugate Addition Reaction: a Very Convenient Platform for Asymmetric Organocatalysis -- 1.5 On the Organization of This Book -- References and Notes -- Chapter 2 Enantioselective Conjugate Addition Reactions via Enamine Activation -- 2.1 Introduction -- 2.1.1 Factors Influencing the Stereocontrol in Michael Additions Proceeding via Enamine Activation -- 2.2 Nitroalkenes as Michael Acceptors -- 2.2.1 Ketones as Michael Donors -- 2.2.2 Aldehydes as Michael Donors -- 2.2.3 Reactions under Non-conventional Methodologies -- 2.3 Enones and Enals as Michael Acceptors -- 2.4 Doubly Activated Olefins as Michael Acceptors -- 2.5 Concluding Remarks -- References and Notes -- Chapter 3 Enantioselective Conjugate Addition Reactions via Iminium Activation -- 3.1 Introduction -- 3.1.1 Factors Influencing the Stereocontrol in Michael Additions Proceeding via Iminium Activation -- 3.2 Michael Reaction -- 3.2.1 α,β-Unsaturated Aldehydes as Michael Acceptors -- 3.2.2 α,β-Unsaturated Ketones as Michael Acceptors -- 3.3 Conjugate Friedel-Crafts Alkylation Reaction -- 3.4 Conjugate Hydrogen Transfer Reaction -- 3.5 Conjugate Addition of Heteroatom-based Nucleophiles -- 3.5.1 Oxa-Michael Reactions -- 3.5.2 Sulfa-Michael Reactions -- 3.5.3 Aza-Michael Reactions -- 3.5.4 Phospha-Michael Reactions -- 3.6 Concluding Remarks -- References and Notes -- Chapter 4 Enantioselective Conjugate Addition Reactions via Hydrogen-bonding Activation -- 4.1 Introduction -- 4.1.1 Some Relevant Aspects Influencing the Stereocontrol in Michael Additions Proceeding via Hydrogen-bonding Activation.

4.2 Conjugate Addition of Stabilized Carbon Nucleophiles -- 4.2.1 Nitroalkenes as Michael Acceptors -- 4.2.2 Enones as Michael Acceptors -- 4.2.3 α,β-Unsaturated Aldehydes as Michael Acceptors -- 4.2.4 Acrylic Acid Derivatives as Michael Acceptors -- 4.2.5 Other Michael Acceptors -- 4.3 Conjugate Friedel-Crafts Reactions -- 4.4 Conjugate Hydrogen-transfer Reactions -- 4.5 Conjugate Addition of Heteronucleophiles -- 4.5.1 Oxa-Michael Reactions -- 4.5.2 Sulfa-Michael Reactions -- 4.5.3 Aza-Michael Reactions -- 4.5.4 Phospha-Michael Reactions -- 4.6 Concluding Remarks -- References and Notes -- Chapter 5 Enantioselective Conjugate Addition Reactions via Phase-transfer Catalysis -- 5.1 Introduction -- 5.1.1 Mechanistic Considerations Regarding Michael Additions Proceeding via Phase-transfer Catalysis -- 5.2 Conjugate Addition of Stabilized Carbon Nucleophiles -- 5.2.1 Enones as Michael Acceptors -- 5.2.2 Acrylic Acid Derivatives as Michael Acceptors -- 5.2.3 α,β-Unsaturated Aldehydes as Michael Acceptors -- 5.2.4 Nitroalkenes as Michael Acceptors -- 5.2.5 Other Michael Acceptors -- 5.3 Conjugate Addition of Heteroatom-centered Nucleophiles -- 5.4 Concluding Remarks -- References and Notes -- Chapter 6 Enantioselective Conjugate Addition Reactions Proceeding via Other Types of Activation -- 6.1 Introduction -- 6.2 Enantioselective Conjugate Addition Reactions Catalyzed by N-heterocyclic Carbenes -- 6.2.1 The Intramolecular Enantioselective Stetter Reaction -- 6.2.2 The Intermolecular Enantioselective Stetter Reaction -- 6.3 Enantioselective Conjugate Addition Reactions Catalyzed by Chiral Brønsted Bases -- 6.3.1 Conjugate Addition of Carbon Nucleophiles -- 6.3.2 Conjugate Addition of Heteroatom-based Nucleophiles -- 6.4 Other Miscellaneous Enantioselective Conjugate Addition Reactions -- 6.5 Concluding Remarks -- References and Notes.

Chapter 7 Enantioselective Cascade Reactions Initiated by Conjugate Addition -- 7.1 Introduction -- 7.2 Cascade Processes Initiated by Conjugate Addition via Enamine Activation -- 7.2.1 Cascade Michael/Aldol Reactions -- 7.2.2 Cascade Michael/Michael Reactions -- 7.2.3 Michael/Michael/Aldol Triple Cascade Reactions -- 7.2.4 Other One-pot Procedures Initiated by Michael Reactions Proceeding under Enamine Activation -- 7.3 Cascade Processes Initiated by Conjugate Addition via Iminium Activation -- 7.3.1 Michael/Aldol Cascade Reactions -- 7.3.2 Michael/Michael Cascade Reactions -- 7.3.3 Michael//α-Alkylation Cascade Reactions -- 7.3.4 Other Cascades Initiated by Michael Reactions Using Stabilized Carbon Nucleophiles -- 7.3.5 Cascades Initiated by Conjugate Friedel-Crafts Reaction -- 7.3.6 Cascades Initiated by Conjugate Hydrogen-transfer Reaction -- 7.3.7 Cascades Initiated by Hetero-Michael Reaction -- 7.4 Cascade Processes Initiated by Conjugate Addition via H-bonding Activation -- 7.4.1 Michael/Henry and Michael/Aza-Henry Cascade Reactions -- 7.4.2 Michael/Michael Cascade Reactions -- 7.4.3 Michael/α-Alkylation Cascade Reactions -- 7.4.4 Other Cascades Initiated by Michael Reactions Using Stabilized Carbon Nucleophiles -- 7.4.5 Cascade Processes Initiated by Hetero-Michael Reactions -- 7.5 Cascade Processes Initiated by Conjugate Addition via Phase-transfer Catalysis -- 7.5.1 Michael/Elimination Cascade Reactions -- 7.5.2 Other Cascades Initiated by Michael Reactions using Stabilized Carbon Nucleophiles -- 7.5.3 Cascade Processes Initiated by Hetero-Michael Reactions -- 7.6 Cascade Processes Initiated by Conjugate Addition via Other Mechanisms of Activation -- 7.6.1 Cascade Processes Initiated by N-heterocyclic Carbene-mediated Conjugate Additions -- 7.6.2 Cascade Processes Initiated by Conjugate Additions Proceeding via Ylide Formation.

7.6.3 Other Miscellaneous Cascade Processes -- 7.7 Concluding Remarks -- References and Notes -- Appendix: Catalysts Referred to in the Text -- Subject Index.
Abstract:
Describes the methodologies for carrying out conjugate addition reactions in a stereoselective way, using small chiral organic molecules as catalysts.
Local Note:
Electronic reproduction. Ann Arbor, Michigan : ProQuest Ebook Central, 2017. Available via World Wide Web. Access may be limited to ProQuest Ebook Central affiliated libraries.
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