The enantioselective cyclopropanation of cinnamyl alcohol (3) to 2-phenylcyclopropanemethanol (4) using (1R,2S)-N-methylephedrine-modified halomethylzinc reagents is reported. Modest (up to 24% ee) enantioselectivites were observed, and a solvent induced reversal of selectivity was noted. These studies demonstrated the potential for chiral zinc species to differentiate olefin enantiofaces in the delivery of methylene to prochiral allylic alcohols.
ASJC Scopus subject areas
- Organic Chemistry