Ontology highlight
ABSTRACT:
SUBMITTER: Salvi L
PROVIDER: S-EPMC2532596 | biostudies-literature | 2007 Dec
REPOSITORIES: biostudies-literature
Journal of the American Chemical Society 20071204 51
A one-pot method for the direct preparation of enantioenriched (Z)-disubstituted allylic alcohols is introduced. Hydroboration of 1-halo-1-alkynes with dicyclohexylborane, reaction with t-BuLi, and transmetalation with dialkylzinc reagents generate (Z)-disubstituted vinylzinc intermediates. In situ reaction of these reagents with aldehydes in the presence of a catalyst derived from (-)-MIB generates (Z)-disubstituted allylic alcohols. It was found that the resulting allylic alcohols were racemic ...[more]