Optically Active Epoxy Diols by Titanium-Catalyzed Oxidation of Enantiomerically Enriched Hydroperoxy and Hydroxy Homoallylic Alcohols

Abstract

Keywords: Optically active epoxy diols / Epoxidation / Titanium catalysis / High diastereoselectivity / Optically active hydroperoxy and hydroxy homoallylic alcohols The Ti-catalyzed epoxidation of optically active (S,S)-hydroperoxy homoallylic alcohols 2 affords the epoxy diol (S,R,S)-4 in high diastereoselectivity (d.r. up to 95:5), while the optically active hydroxy homoallylic alcohols (R,R)-3 are epoxidized by the β-hydroperoxy alcohol 5 under titanium catalysis to the corresponding epoxy (R,S,R)-diol 4 in a diastereomericEur.