Cu(II)-Catalyzed Enantioselective β‑Boration of β‑Trifluoromethyl, β,β-Disubstituted Enones and Esters: Construction of a CF3- and Boron-Containing Quaternary Stereocenter

A highly enantioselective Cu­(II)-catalyzed borylative reaction of β-trifluoromethyl β,β-disubstituted enones was developed, which provide a facile access to a variety of chiral alkylboronic esters with a quaternary stereocenter including both a trifluoromethyl group and a boron group. Meanwhile, CF...

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Bibliographic Details
Published in:ACS catalysis 2018-09, Vol.8 (9), p.8318-8323
Main Authors: Liu, Bing, Wu, Hai-Hong, Zhang, Junliang
Format: Article
Language:English
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Summary:A highly enantioselective Cu­(II)-catalyzed borylative reaction of β-trifluoromethyl β,β-disubstituted enones was developed, which provide a facile access to a variety of chiral alkylboronic esters with a quaternary stereocenter including both a trifluoromethyl group and a boron group. Meanwhile, CF3-contained tertiary alcohol derivatives were obtained in high yield with the maintained ee value via one-pot methodology. The reactions proceed smoothly under mild reaction conditions, providing expedient access to construct chiral alkylboronic esters in well-functional group tolerances, good yields, diversity conversion, and high enantioselectivities. The appropriate SDE test via achiral chromatography illustrated that the results presented here were reliable.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b02543