Stereoselective Conjugate Addition of Organoaluminum Chlorides to α,β-Unsaturated Carboxylic Acid Derivatives

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Abstract
Organoaluminum chlorides react smoothly with α,β-unsaturated N-acyloxazolidinones providing chiral β-branched carboxylic acid derivatives. An unexpected contrast between the mode of reaction of dimethylaluminum chloride and that of the higher homologues is observed. While diethylaluminum chloride and its higher homologues react with the acceptors at low temperature via a polar pathway, dimethylaluminum chloride requires activation by UV-light or radical initiation under otherwise identical conditions. With bicyclic oxazolidinones derived from galactosamine a high stereoselection is accomplished in the formation of the branched carboxylic acid derivative.

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