Synthesis of Optically Active β,γ-Epoxy Alcohols and Secondary Allylic Alcohols via Diastereoselective Addition of α-Trimethylsilyl-α,β-epoxy Aldehydes with Organometallic Compounds

Article abstract of DOI:10.1021/jo00374a047

Optically active α-trimethylsilyl-α,β-epoxy aldehydes 3 react with various Grignard reagents or organolithium compounds highly stereoselectively to give erythro adducts 4, which can be readily converted into β,γ-epoxy secondary alcohols 1 or secondary allylic alcohols 2.