Copper-Catalyzed Remote Enantioselective Sulfonylation of Yne-Allylic Esters with Sodium Sulfinates

被引:21
|
作者
Li, Meng-Die [1 ]
Wang, Zi-Han [1 ]
Zhu, Hui [1 ]
Wang, Xin-Ru [1 ]
Wang, Jia-Run [1 ]
Lin, Tao-Yan [1 ]
机构
[1] Huaibei Normal Univ, Sch Chem & Mat Sci, Key Lab Green & Precise Synthet Chem & Applicat, Minist Educ, Huaibei 235000, Anhui, Peoples R China
关键词
Asymmetric Catalysis; Copper; Remote Substitution; Sulfur; ASYMMETRIC PROPARGYLIC SUBSTITUTION; FORMAL 3+2 CYCLOADDITION; BETA-KETOESTERS; AMINES; QUATERNARY; ALCOHOLS; ETHERIFICATION; CONSTRUCTION; AMINATION; ACETATES;
D O I
10.1002/anie.202313911
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Impressive progress has been made in the copper-catalyzed asymmetric propargylic substitution (APS) reaction, but its use in remote asymmetric yne-allylic substitution remains a challenging topic. Herein, we report the first remote enantioselective copper-catalyzed sulfonylation of yne-allylic esters with sodium sulfinates. The reaction is assumed to occur via a copper-vinylvinylidene species as the key reactive intermediate. The use of readily available starting materials, the mild reaction conditions, and the excellent regio-, enantio- and stereoselectivity, as well as broad substrate scope (>70 examples), show the practicality and attractiveness of this method.
引用
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页数:6
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