Synthesis of fluorocyclopropanes via the enantioselective cyclopropanation of fluoro-substituted allylic alcohols using zinc carbenoids

Abstract

Cyclopropanation reactions using zinc carbenoids are a powerful means to access cyclopropanes. Described herein is an enantioselective version of the reaction using zinc reagents and a chiral dioxaborolane ligand in the generation of fluorocyclopropanes. Readily available 2- and 3-fluoroallylic alcohols were efficiently cyclopropanated in high yields and excellent enantioselectivities. This method provides access to a variety of structurally diverse chiral fluorocyclopropanes that can be used as useful chiral building blocks.