Synthesis of allenic diols by samarium, diiodide-promoted coupling between alkynyloxiranes and ketones

Article abstract of DOI:10.1016/S0040-4020(98)00110-0

The SmI₂-mediated reductive coupling between alkynyloxiranes and ketones provides a new route to 2,3-pentadiene-1,5-diols. The preferred stereochemistry observed in the coupling products is the result of the new C- C bond forming anti with respect to the opening epoxide ring. Yields and diastereoselectivities are dependent on the alkynyloxirane substitution pattern.