Synthesis of Functionalized Epoxides by Copper-Catalyzed Alkylative Epoxidation of Allylic Alcohols with Alkyl Nitriles

A 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.


Published in:
Organic Letters, 17, 8, 1890-1893
Year:
2015
Publisher:
Washington, Amer Chemical Soc
ISSN:
1523-7052
Laboratories:




 Record created 2015-05-07, last modified 2018-03-17


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