Copper-Catalyzed Asymmetric Synthesis

by Alexakis, Alexandre; Krause, Norbert; Woodward, Simon

• ISBN13: 9783527332045
• ISBN10: 3527332049
• Edition: 1st
• Format: Hardcover
• Copyright: 2014-03-31
• Publisher: Wiley-VCH

Summary

This book reflects the increasing interest among the chemical synthetic community in the area of asymmetric copper-catalyzed reactions, and introduces readers to the latest, most significant developments in the field.

The contents are organized according to reaction type and cover mechanistic and spectroscopic aspects as well as applications in the synthesis of natural products. A whole chapter is devoted to understanding how primary organometallics interact with copper to provide selective catalysts for allylic substitution and conjugate addition, both of which are treated in separate chapters. Another is devoted to the variety of substrates and experimental protocols, while an entire chapter covers the use on non-carbon nucleophiles. Other chapters deal with less-known reactions, such as carbometallation or the additions to imines and related systems, while the more established reactions cyclopropanation and aziridination as well as the use of copper (II) Lewis acids are warranted their own special chapters. Two further chapters concern the processes involved, as determined by mechanistic studies. Finally, a whole chapter is devoted to the synthetic applications.

This is essential reading for researchers at academic institutions and professionals at pharmaceutical or agrochemical companies.

Author Biography

Alexandre Alexakis is a Professor of Organic Chemistry at the University of Geneva, Switzerland. He graduated from Paris VI University in 1970 and received his PhD in 1975. After a postdoctoral stay at Johns Hopkins University, Baltimore (USA), he joined the CNRS at Pierre et Marie Curie University in 1977, being appointed Directeur de Recherche in 1985. In 1994 he was awarded the Silver Medal of the CNRS. In 1996 he moved from CNRS to Pierre et Marie Curie University as full Professor (1st class), then to the University of Geneva in 1998. In 2002 he was awarded the Novartis Lectureship Award. His research focuses on asymmetric synthesis and methodologies, using both metal catalysts, particularly copper reagents, and non-metallic catalysts (organocatalysis). He is the author of 300 articles.

Simon Woodward is a Professor in Synthetic Organic Chemistry at Nottingham University, UK. He has been Director of both The European Ligand Bank (a facility for the exchange of ligand ideas between groups interested in selective catalysis, 2004-present) and an International Marie Curie Ph.D. School (INDAC-CHEM, 2007-2010) in "Catalysis of Organic Reactions" encompassing the Universities of Nottingham, Geneva, Sassari and Dortmund. He is also the Chair of the European Cooperation in Science and Technology (COST) action D40 in "Innovative Catalysis" (2006-2011) and a member action CM0903 in "Biomass Utilisation". The flexibility of his research group is highly strengthened by extensive collaborative with over 20 other groups, both throughout Europe and beyond, involved in the selective catalysis of organic reactions. He has authored over 110 publications in the areas of organic methodology, organometallic chemistry, and selective/asymmetric catalysis.

Norbert Krause graduated from Technical University of Braunschweig, Germany, in 1984 and received his PhD in 1986. After postdoctoral stays at the ETH Z?rich and Yale University, he joined the Technical University of Darmstadt and obtained his Habilitation in 1993. In 1994, he moved to the University of Bonn as Associate Professor, before being appointed to his present position at Dortmund University of Technology as Full Professor in 1998. He was a Fellow of the Japan Society for the Promotion of Science (2003 and 2009), and Guest Professor at the Universit? Catholique de Louvain, Belgium (2007), at the University of California, Santa Barbara, USA (2009), and at the ?cole Sup?rieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI), France (2009). Since 2006, he is a member of the Editorial Board of the European Journal of Organic Chemistry. His review on "Recent Advances in Catalytic Enantioselective Michael Additions" was the World's Most Cited Chemistry Paper in Nov. 2002. His research focuses on the stereoselective synthesis and transformation of functionalized allenes, taking advantage of coinage metal (copper, silver, and gold) catalysis.

Table of Contents

Introduction
The Primary Organometallic in Copper Catalyzed Reactions
Asymmetric Conjugate Addition (1,4)
Conjugate Addition to Extended Michael Acceptors
Asymmetric Allylic Alkylation
Opening of Epoxides and Related Systems
Non-Carbon Nucleophiles
CuH in Asymmetric Reductions
Asymmetric Cyclopropanation Reactions
Copper in Lewis Acid Catalyzed Reactions
Mechanistic Aspects of Copper Catalyzed Reactions
Spectroscopic Aspects
Applications to the Synthesis of Natural Products