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

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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