Harnessing the elusive 1,4-reduction of vinyl epoxides through copper catalysis

This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acscatal.9b02005We present an efficient strategy for the formal 1,4-reduction of vinyl epoxides that does not require superstoichiometric amounts of a strong reductant. Using a readily available copper catalyst and a diboron compound, a wide variety of enantioenriched allylic alcohols have been prepared. Additionally, epoxyenynes have been reduced in a 1,4-manner to selectively afford skipped enynes or skipped dienes.We thank the European Research Council (ERC-337776) and MINECO (CTQ2016-78779-R) for financial suppor