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Highly Diastereo- and Enantioselective Copper-Catalyzed Domino Reduction/Aldol Reaction of Ketones with Methyl Acrylate

Julia Deschamp, Olivier Chuzel, Jérôme Hannedouche, Olivier Riant*

*Unité de chimie organique et médicinale Université catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve, Belgium, Email: riantchim.ucl.ac.be

J. Deschamp, O. Chuzel, J. Hannedouche, O. Riant, Angew. Chem. Int. Ed., 2006, 45, 1292-1297.

DOI: 10.1002/anie.200503791 (free Supporting Information)


Abstract

A new strategy for the catalytic asymmetric aldol reaction of ketones was developed that relies on a chiral copper(I) complex-catalyzed domino reduction/aldol reaction sequence in the presence of phenylsilane.

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Key Words

aldol reaction, copper, enantioselectivity, enolates, hydrosilylation, phenylsilane, β-hydroxy esters


ID: J06-Y2006-430