This book, unique in its field, is a comprehensive description of all the methodologies reported for carrying out conjugate addition reactions in a stereoselective way, using small chiral organic molecules as catalysts (organocatalysts). In the last 3-4 years, this has been a rapidly growing field in organic chemistry, and many papers have appeared reporting excellent protocols for carrying out these highly efficient transformations that compete well with other classical approaches using transition metal catalysts. A particularly attractive feature of this transformation relies upon the fact that the conjugate addition (Michael and Hetero-Michael reactions) is an extraordinarily effective means to initiate cascade processes which result in the formation of complex molecules from very small and simple starting blocks. The book, written by noted experts, covers all recent advances in this hot topic, and provides a good state-of-the-art review for organic chemists working in this field and all those who wish to start projects in this area.

Introduction	p. 1
Organocatalysis: an Emerging Field	p. 1
Historical Evolution of Asymmetric Organocatalysis	p. 5
Types of Organocatalysts	p. 9
The Conjugate Addition Reaction: a Very Convenient Platform for Asymmetric Organocatalysis	p. 11
On the Organization of This Book	p. 12
References and Notes	p. 13
Enantioselective Conjugate Addition Reactions via Enamine Activation	p. 18
Introduction	p. 18
Factors Influencing the Stereocontrol in Michael Additions Proceeding via Enamine Activation	p. 20
Nitroalkenes as Michael Acceptors	p. 23
Ketones as Michael Donors	p. 23
Aldehydes as Michael Donors	p. 33
Reactions under Non-conventional Methodologies	p. 42
Enones and Enals as Michael Acceptors	p. 45
Doubly Activated Olefins as Michael Acceptors	p. 50
Concluding Remarks	p. 56
References and Notes	p. 56
Enantioselective Conjugate Addition Reactions via Iminium Activation	p. 62
Introduction	p. 62
Factors Influencing the Stereocontrol in Michael Additions Proceeding via Iminium Activation	p. 64
Michael Reaction	p. 66
¿,ß-Unsaturated Aldehydes as Michael Acceptors	p. 67
¿,ß-Unsaturated Ketones as Michael Acceptors 80
Conjugate Friedel-Crafts Alkylation Reaction	p. 87
Conjugate Hydrogen Transfer Reaction	p. 91
Conjugate Addition of Heteroalom-based Nucleophiles	p. 94
Oxa-Michael Reactions	p. 94
Sulfa-Michael Reactions	p. 97
Aza-Michael Reactions	p. 99
Phospha-Michael Reactions	p. 103
Concluding Remarks	p. 106
References and Notes	p. 106
Enantioselective Conjugate Addition Reactions via Hydrogen-bonding Activation	p. 112
Introduction	p. 112
Some Relevant Aspects Influencing the Stereocontrol in Michael Additions Proceeding via Hydrogen-bonding Activation	p. 116
Conjugate Addition of Stabilized Carbon Nucleophiles	p. 119
Nitroalkenes as Michael Acceptors	p. 120
Enones as Michael Acceptors	p. 139
¿,ß-Unsaturated Aldehydes as Michael Acceptors	p. 146
Acrylic Acid Derivatives as Michael Acceptors	p. 149
Other Michael Acceptors	p. 152
Conjugate Friedel-Crafls Reactions	p. 159
Conjugate Hydrogen-transfer Reactions	p. 164
Conjugate Addition of Heteronucleophiles	p. 167
Oxa-Michael Reactions	p. 168
Sulfa-Michael Reactions	p. 171
Aza-Michael Reactions	p. 174
Phospha-Michael Reactions	p. 177
Concluding Remarks	p. 179
References and Notes	p. 180
Enantioselective Conjugate Addition Reactions via Phase-transfer Catalysis	p. 187
Introduction	p. 187
Mechanistic Considerations Regarding Michael Additions Proceeding via Phase-transfer Catalysis	p. 190
Conjugate Addition of Stabilized Carbon Nucleophiles	p. 193
Enones as Michael Acceptors	p. 193
Acrylic Acid Derivatives as Michael Acceptors	p. 206
¿,ß-Unsaturated Aldehydes as Michael Acceptors	p. 212
Nitroalkenes as Michael Acceptors	p. 214
Other Michael Acceptors	p. 215
Conjugate Addition of Heteroatom-cenlered Nucleophiles	p. 218
Concluding Remarks	p. 219
References and Notes	p. 219
Enantioselective Conjugate Addition Reactions Proceeding via Other Types of Activation	p. 222
Introduction	p. 222
Enantioselective Conjugate Addition Reactions Catalyzed by N-heterocycIic Carbenes	p. 223
The Intramolecular Enantioselective Stetter Reaction	p. 225
The Intermolecular Enantioselective Stetter Reaction	p. 230
Enantioselective Conjugate Addition Reactions Catalyzed by Chiral Brensted Bases	p. 233
Conjugate Addition of Carbon Nucleophiles	p. 234
Conjugate Addition of Heteroatom-based Nucleophiles	p. 236
Other Miscellaneous Enantioselective Conjugate Addition Reactions	p. 238
Concluding Remarks	p. 241
References and Notes	p. 241
Enantioselective Cascade Reactions Initiated by Conjugate Addition	p. 244
Introduction	p. 244
Cascade Processes Initiated by Conjugate Addition via Enamine Activation	p. 245
Cascade Michael/Aldol Reactions	p. 245
Cascade Michael/Michael Reactions	p. 248
Michael/Michael/Aldol Triple Cascade Reactions	p. 250
Other One-pot Procedures Initiated by Michael Reactions Proceeding under Enamine Activation	p. 254
Cascade Processes Initiated by Conjugate Addition via Iminium Activation	p. 257
Michael/Aldol Cascade Reactions	p. 257
Michael/Michael Cascade Reactions	p. 266
Michael//$$$-Alkylation Cascade Reactions	p. 273
Other Cascades Initiated by Michael Reactions Using Stabilized Carbon Nucleophiles	p. 276
Cascades Initiated by Conjugate Friedel-Crafts Reaction	p. 279
Cascades Initiated by Conjugate Hydrogen-transfer Reaction	p. 283
Cascades Initiated by Hetero-Michael Reaction	p. 287
Cascade Processes Initiated by Conjugate Addition via H-bonding Activation	p. 299
Michael/Henry and Michael/Aza-Henry Cascade Reactions	p. 300
Michael/Michael Cascade Reactions	p. 302
Michael/a-Alkylation Cascade Reactions	p. 304
Other Cascades Initiated by Michael Reactions Using Stabilized Carbon Nucleophiles	p. 306
Cascade Processes Initiated by Hetero-Michael Reactions	p. 308
Cascade Processes Initiated by Conjugate Addition via Phase-transfer Catalysis	p. 311
Michael/Elimination Cascade Reactions	p. 311
Other Cascades Initiated by Michael Reactions using Stabilized Carbon Nucleophiles	p. 315
Cascade Processes Initiated by Hetero-Michael Reactions	p. 316
Cascade Processes Initiated by Conjugate Addition via Other Mechanisms of Activation	p. 318
Cascade Processes Initiated by N-heterocyclic Carbene-mediated Conjugate Additions	p. 318
Cascade Processes Initiated by Conjugate Additions Proceeding via Ylide Formation	p. 319
Other Miscellaneous Cascade Processes	p. 321
Concluding Remarks	p. 322
References and Notes	p. 323
Appendix: Catalysts Referred to in the Text	p. 330
Subject Index	p. 340
Table of Contents provided by Ingram. All Rights Reserved.

What is included with this book?

The New copy of this book will include any supplemental materials advertised. Please check the title of the book to determine if it should include any access cards, study guides, lab manuals, CDs, etc.

The Used, Rental and eBook copies of this book are not guaranteed to include any supplemental materials. Typically, only the book itself is included. This is true even if the title states it includes any access cards, study guides, lab manuals, CDs, etc.

Amazon no longer offers textbook rentals. We do!

Amazon no longer offers textbook rentals. We do!

We're the #1 textbook rental company. Let us show you why.

Organocatalytic Enantioselective Conjugate Addition Reactions

9781849730242

1849730245

Supplemental Materials

Summary

Table of Contents

Supplemental Materials

Rewards Program