Aldolisation of a carbohydrate enolate: stereochemical outcome and X-ray crystal structure determination of an aldol product

Abstract

Reaction of acetaldehyde and propionaldehyde with the carbohydrate derived enolate (2) occurs with excellent diastereofacial selectivity on the enolate but modest facial selectivity on the aldehyde, giving aldols (4) and (5) in good yield; the major isomer (4a) was reduced to the diol (7), the structure of which has been determined by X-ray crystal structure analysis.