Diastereoselective Synthesis of 1,2,3-Substituted Potassium Cyclopropyl Trifluoroborates via an Unusual Zinc-Boron Exchange

Abstract

Diastereoselective cyclopropanation of an allylic alcohol with a gem-dizinc carbenoid followed by an unusual zinc-boron exchange and further treatment with excess KHF₂ afforded 1,2,3-syn-cis-substituted cyclopropyl trifluoroborates in 58-63% overall yields. The potassium cyclopropyl trifluoroborates underwent ­Suzuki-Miyaura cross-coupling reactions to give 1,2,3-functionalized cyclopropanes in good yields. Finally, an oxidation-epimerization sequence gave access to 1,2,3-trans-substituted cyclopropyl trifluoroborate.

carbenoids - zinc - cycloaddition - cross-coupling - dia­stereoselectivity

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