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

被引:31
作者
Liu, Bing [1 ]
Wu, Hai-Hong [1 ]
Zhang, Junliang [2 ]
机构
[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 3663 N Zhongshan Rd, Shanghai 200062, Peoples R China
[2] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai 200438, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric copper catalysis; enones; conjugate addition; boration; CF3-quaternary stereocenter; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; TERTIARY ORGANOBORONIC ESTERS; N-HETEROCYCLIC CARBENES; CONJUGATE ADDITIONS; ASYMMETRIC-SYNTHESIS; SELF-DISPROPORTIONATION; CATALYZED HYDROBORATION; STEREOGENIC CENTERS; UNSATURATED ESTERS; DIRECT GENERATION;
D O I
10.1021/acscatal.8b02543
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A highly enantioselective Cu(II)-catalyzed borylative reaction of beta-trifluoromethyl beta,beta-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.
引用
收藏
页码:8318 / 8323
页数:11
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