Copper-catalyzed Asymmetric Conjugate Addition to Challenging Michael Acceptors and Synthesis of Relevant Target Molecules

Authors

  • Ludovic Gremaud SCS-Metrohm Foundation Award for best oral presentation, University of Geneva Department of Organic Chemistry Quai Ernest-Ansermet, 30 CH-1211 Genève 4, Switzerland
  • Laëtitia Palais University of Geneva Department of Organic Chemistry Quai Ernest-Ansermet, 30 CH-1211 Genève 4, Switzerland
  • Alexandre Alexakis University of Geneva Department of Organic Chemistry Quai Ernest-Ansermet, 30 CH-1211 Genève 4, Switzerland. alexandre.alexakis@unige.ch

DOI:

https://doi.org/10.2533/chimia.2012.196

Keywords:

Asymmetric conjugate addition, Copper, Organometallic reagents, α,β-unsaturated aldehydes, β,γ-unsaturated-α-ketoesters

Abstract

We report herein the enantioselective Cu-catalyzed conjugate addition of organometallic reagents to sensitive Michael acceptors and their application to the synthesis of relevant target molecules. This is one of the most important methodologies to form a C–C bond in an enantioselective manner. A wide range of ?,?-unsaturated aldehydes and ?,?-unsaturated-?-ketoesters has been successfully used. Reactivity, regio- and enantioselectivities were strongly dependent on the reaction conditions, therefore moderate to very good results were obtained. Furthermore, ?-substituted-?-ketoesters were used as chiral building blocks for further derivatization with complete retention of the chiral information to obtain key compounds.

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Published

2012-04-25

How to Cite

[1]
L. Gremaud, L. Palais, A. Alexakis, Chimia 2012, 66, 196, DOI: 10.2533/chimia.2012.196.