Addition of organolithium reagents to some carbohydrate enones

Article abstract of DOI:10.1016/S0040-4020(97)00253-6

Addition of organolithium reagents to die sugar enones: alkyl 2,3,6-trideoxy-α-L- and 2,3-dideoxy-α- D-hex-2-enopyranosid-4-ulose has been examined. Butyl, benzyl and 2,5-dimethoxy-4-methylphenyllithium add, with increasing stereoselectivity, to the carbonyl group of the α,β-unsaturated ketosugars, whereas 2,5-dimethoxybenzyllithium undergoes stereospecific conjugate addition and 1,2-addition in die ratio of 1.7:1. The structure of the resultant carbinols is based on X-ray crystallographic evidence.