Two highly enantio- and diastereoselective one-pot procedures for the synthesis of epoxy alcohols with up to three contiguous stereocenters will be presented. Route one involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective epoxidation or asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective epoxidation. The second route uses a catalyst we have developed for the asymmetric addition of alkyl groups to enones followed by epoxidation. The scope of the asymmetric addition of alkyl, vinyl, and aryl groups to ketones will be discussed.
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