Stereoselective Conjugate Addition of Mixed Organoaluminum Reagents to α,β-Unsaturated N-Acyloxazolidinones Derived from Carbohydrates

Stephan Elzner; Steffen Maas; Stefan Engel; Horst Kunz

doi:10.1055/s-2004-831173

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Synthesis 2004(13): 2153-2164
DOI: 10.1055/s-2004-831173

PAPER

Stereoselective Conjugate Addition of Mixed Organoaluminum Reagents to α,β-Unsaturated N-Acyloxazolidinones Derived from Carbohydrates

Stephan Elzner^a, Steffen Maas^a,b, Stefan Engel^a,b, Horst Kunz*^a
^a Institut für Organische Chemie, Johannes-Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
Fax: +49(613)13924786; e-Mail: hokunz@mail.uni-mainz.de;
^b BASF AG, 67056 Ludwigshafen, Germany

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Publication History

Received 2 April 2004
Publication Date:
17 August 2004 (online)

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Abstract

The stereoselective synthesis of β-branched carboxylic acid derivatives was accomplished by conjugate addition of mixed organoaluminum reagents to chiral α,β-unsaturated N-acyloxazolidinones. Mixed organoaluminum reagents were generated in situ by transmetalation of Grignard or organolithium compounds with methylaluminum dichloride. Efficient stereocontrol was achieved using different bicyclic glycosamine-derived oxazolidinones, yielding alternatively (R)- or (S)-configured β-branched carboxylic acid derivatives.

Key words

stereoselective Michael additions - organoaluminum compounds - chiral carboxylic acids - carbohydrates - auxiliaries

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