Enantioselective Copper-Catalyzed 1,5-Cyanotrifluoromethylation of Vinylcyclopropanes

A copper-catalyzed enantioselective 1,5-cyanotrifluoromethylation of vinylcyclopropanes has been developed using a radical relay strategy. This asymmetric reaction has demonstrated high enantioselective control, broad substrate scope, and mild conditions. Initiated by the in situ generated CF3 radic...

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Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (20), p.8256-8260
Main Authors: Zhang, Zi-Qi, Meng, Xiang-Yu, Sheng, Jie, Lan, Quan, Wang, Xi-Sheng
Format: Article
Language:English
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Summary:A copper-catalyzed enantioselective 1,5-cyanotrifluoromethylation of vinylcyclopropanes has been developed using a radical relay strategy. This asymmetric reaction has demonstrated high enantioselective control, broad substrate scope, and mild conditions. Initiated by the in situ generated CF3 radical from Togni’s reagent, this method offers a new solution for remote enantioselective bifunctionalization of alkenes and thus provides a straightforward way for the synthesis of chiral CF3-containing internal alkenylnitriles.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03012