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Synthesis 2004(13): 2153-2164
DOI: 10.1055/s-2004-831173
DOI: 10.1055/s-2004-831173
PAPER
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Conjugate Addition of Mixed Organoaluminum Reagents to α,β-Unsaturated N-Acyloxazolidinones Derived from Carbohydrates
Further Information
Received
2 April 2004
Publication Date:
17 August 2004 (online)
Publication History
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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