Bunescu, AlaWang, QianZhu, Jieping2015-05-072015-05-072015-05-07201510.1021/acs.orglett.5b00571https://infoscience.epfl.ch/handle/20.500.14299/113747WOS:000353314800019A copper-catalyzed oxyalkylation of allylic alcohols using nonactivated alkyl nitriles as reaction partners was developed. A sequence involving generation of an alkyl nitrile radical followed by its addition to a double bond and a copper-mediated formation of C(sp3)−O bond was proposed to account for the reaction outcome. The protocol provided an efficient route to functionalized tri- and tetrasubstituted epoxides via formation of a C(sp3)−C(sp3) and a C(sp3)−O bond with moderate to excellent diastereoselectivity.text::journal::journal article::research article