Abstract
Bis(cis-1-alkenyl)methanols 2a and b were monoepoxidized by a 1:1:1 mixture of R tert OOH, an optically active tartaric acid derivative, and a Zr(IV) alkoxide. This provided epoxy alcohols syn-1a,b with perfect diastereoselectivity. These compounds are the minor products of analogous Ti(IV)-mediated epoxidations. The ee of epoxy alcohol syn-1a was increased up to 99% when less enantioenriched material was overoxidized under the reaction conditions (→ up to 66% bisepoxy alcohol syn,syn-5).
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