Abstract
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 diastereomeric ratio up to > 99:1. This high diastereoselectivity is rationalized in terms of a rigid template for the oxygen transfer, in which the hydroperoxy alcohol 2 or 5 is ligated tridentately and the diol 3 bound bidentately to the titanium metal. Through these oxidative routes, both enantiomeric epoxy diols 4 are conveniently accessible.
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