Lewis acid-promoted cascade reactions of cyclopropenes: a unified approach to stereoselective synthesis of cyclic ethers and oxaspirolactones†

Abstract

Lewis acid-promoted 5/6-exo trig hydroalkoxylation/reduction cascade of ω-hydroxy cyclopropenes gave expeditious, stereoselective access to THF/THP derivatives. Monoester substituted ω-hydroxy cyclopropenes on treatment with catalytic Bi(OTf)₃ lead to [5,5]/[6,5] oxaspirocyclic lactones. This unified strategy relies on generation of transient donor–acceptor (D–A) cyclopropanes from ω-hydroxy cyclopropene precursors. This approach allows for the sequential addition of two nucleophiles in a ‘one pot’ process for the synthesis of THP derivatives. The utility of this methodology is demonstrated in the stereoselective synthesis of a homologue of (±)-civet.