Comprehensive Enantioselective Organocatalysis

Catalysts, Reactions, and Applications

Dalko, Peter I. (Editor)

1. Edition October 2013
XL, 1160 Pages, Hardcover
1420 Pictures (20 Colored Figures)
60 tables
Handbook/Reference Book

ISBN: 978-3-527-33236-6

Wiley-VCH, Weinheim

Wiley Online Library Content Sample Chapter Index

Short Description

Written by pioneers of the field, this much-needed handbook reflects the developments of the past 5 years, comprehensively covering all relevant catalyst systems, as well as key strategies, reaction types, and important applications in total synthesis.

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Further versions

Structured in three parts this manual recollects efficient organocatalytic transformations around clear principles that meet actual standard in asymmetric synthesis. Chapters were written by acknowledged leaders of the organocatalysis field, and are presented in a concise way. Volume 1: Privileged Catalysts gives insight to readers to the continuously increasing variety of catalysts, and the relatively complex interactions that make organocatalytic reactions selective. An appendix recollects catalyst structures with the adequate cross-references. Volume 2: Activations covers the fundamental activation types (non-covalent and covalent activations) and helps understanding the importance of physical parameters, and in particular, the role of water, that influences reactivity and selectivity. Volume 3: Reactions and Applications highlights transformations by reaction types. The final part of this volume is dedicated to application in multistep synthesis and industrial applications.

Considering the ever increasing interest in the organocatalysis field, the book aims addressing to a large audience: to academic, and, industrial researchers, students and teachers who are interested in synthetic organic chemistry at advanced level. This book provides non-specialists with an introduction to the topic as well as serving as a valuable source for newcomers and researchers searching for an up-to-date and comprehensive overview of this promising area of synthetic organic chemistry.

VOLUME ONE - Privileged Catalysts

PART I: AMINO ACID-DERIVED CATALYSTS
Proline-Related Secondary Amine Catalysts and Applications
TMS-Prolinol Catalyst in Organocatalysis
Non-Proline Amino Acid Catalysts
Chiral Imidazolidinone (MacMillan's Catalyst)
Oligopeptides as Modular Organocatalytic Scaffolds

PART II: NON-AMINO ACID-DERIVED CATALYSTS
Cinchonas and Cupreidines
Chiral C2 Catalysts
Planar Chiral Catalysts
Dynamic Approaches towards Catalyst Discovery

VOLUME TWO - Activations

PART I: ASYMMETRIC CATALYSIS WITH NON-COVALENT INTERACTIONS
Bronsted Acids
Bronsted Acids: Chiral Phosphoric Acid Catalysts in Asymmetric Synthesis
Bronsted Acids: Chiral (Thio)urea Derivatives
Bronsted Bases
Chiral Onium Salts (Phase-Transfer Reactions)
Lewis Bases
Lewis Acids

PART II: ASYMMETRIC CATALYSIS WITH COVALENT INTERACTIONS
Rationalizing Reactivity and Selectivity in Aminocatalytic Reactions
Carbene Catalysts
Oxides and Epoxides
Ylides

PART III: TUNING CATALYST ACTIVITY AND SELECTIVITY BY THE REACTION MEDIUM AND CONDITIONS
"Non-Classical" Activation of Organocatalytic Reactions (Pressure, Microwave Irradiation)
Ionic Liquid Organocatalysts
Polymer and Mesoporous Material Supported Organocatalysts
Water in Organocatalytic Reactions

VOLUME THREE - Reactions and Applications

PART I: ALPHA-ALKYLATION AND HETEROATOM FUNCTIONALIZATION
SN2-Type Alpha-Alkylation and Allylation Reactions
Alpha-Alkylation by SN1-Type Reactions
Alpha-Heteroatom Functionalization of Carbonyl Compounds

PART II: NUCLEOPHILE ADDITION TO C=X BONDS
Aldol and Mannich-Type Reactions
Additions of Nitroalkyls and Sulfones to C=X
Hydrocyanation and Strecker Reactions
The Morita-Baylis-Hillman (MBH) and Hetero-MBH Reactions
Reduction of C=O and C=N

PART III: NUCLEOPHILE ADDITION TO C=C BONDS
Addition to Alpha, Beta-Unsaturated Aldehydes and Ketones
Addition to Nitroolefins and Vinyl Sulfones
Organocatalyzed Asymmetric Arylation and Heteroarylation Reactions

PART IV: RING-FORMING REACTIONS
Intramolecular Reactions
Formation of 3-, 4- and 5-Membered Cycles by Intermolecular Reactions
Diels-Alder and Hetero-Diels-Alder Reactions

PART V: INCREASING COMPLEXITY
Organocatalytic Radical and Electron Transfer Reactions
Organocatalytic Sigmatropic Reactions
Regio- and Position Selective Reactions and Desymmetrizations
Three or More Components Reactions (Single Catalyst Systems)
Multi-Catalyst Systems
Organocatalysis in Total Synthesis

Peter I. Dalko studied chemistry at the Budapest Technical University (Hungary) and graduated from Paris XI University (France) under the supervision of the late Stephan D. Géro. After undertaking postdoctoral researches with the late Sir Derek H. Barton at TAMU (USA) and Yoshito Kishi at Harvard University he is now a Research Director at the French Scientific Research Council (CNRS) at the Medical Faculty of the Sorbonne Paris Cité (France). His research is focused on total synthesis of structurally complex natural products, development of organocatalytic reactions for synthesis and developing microand nanoscale technologies for biomedical researches.

P. I. Dalko, CNRS, Uni Paris Descartes, Paris, France