Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C–O reduction approach

Abstract

Unsaturated cyclic ethers can be mildly and selectively reduced with catalytic amounts of B(C₆F₅)₃ in the presence of an alkylsilane. The allylic position is preferentially reduced with minimal or no scrambling of olefin geometry. For electronically equivalent substrates, steric factors guide the reducing agent to the least substituted site.