A selective and efficient protocol for the catalytic asymmetric cyclopropanation of allylic alcohols has been developed. The reaction involves preformation of the ethylzinc alkoxide of the alcohol and reaction with the Furukawa/Simmons-Smith reagent. Zinc iodide has been shown to have a beneficial effect on the rate and enantioselectivity of the reaction. The structural variability in the allylic alcohol as been examined and the reaction was found to proceed smoothly with both E and Z- allylic alcohols with one or two β-substituents, but α-substitution was not well tolerated.
ASJC Scopus subject areas
- Chemical Engineering(all)