Copper-Catalysed Domino Silylative Aldol Reaction Leading to Stereocontrolled Chiral Quaternary Carbons

Authors

  • Alexandre Welle,

    1. Unité de chimie organique et médicinale Université Catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve (Belgium), Fax: (+)1047-4168
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  • Dr. Julien Petrignet,

    1. Unité de chimie organique et médicinale Université Catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve (Belgium), Fax: (+)1047-4168
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  • Prof. Bernard Tinant,

    1. Unité de chimie structurale et des mécanismes réactionnels Université Catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve (Belgium)
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  • Prof. Johan Wouters,

    1. Unité de Chimie Physique Théorique et Structurale, Facultés Universitaires Notre-Dame de la Paix, Rue de Bruxelles 61, 5000 Namur (Belgium)
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  • Prof. Olivier Riant

    1. Unité de chimie organique et médicinale Université Catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve (Belgium), Fax: (+)1047-4168
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Errata

This article is corrected by:

  1. Errata: Corrigendum: Copper-Catalysed Domino Silylative Aldol Reaction Leading to Stereocontrolled Chiral Quaternary Carbons Volume 17, Issue 44, 12227, Article first published online: 17 October 2011

Abstract

original image

Asymmetric aldol reaction: A domino silylation–aldol reaction between enoyloxazolidinones and various aldehydes has been developed (see scheme). The process catalysed by a copper complex in the presence of a borosilane led to high diastereoselectivities. Yields between 59 and 90 % and d.r. values between 78:22 to 95:5 were obtained. When methacryloyloxazolidinones were used, a controlled chiral quaternary carbon was generated. BPin=4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl.

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