Kinetic Resolution and Dynamic Kinetic Resolution of γ-Aryl-Substituted Butenolides via Copper-Catalyzed 1,4-Hydroboration

被引：3
|
作者：
Lee, Soyeon [1 ,2 ]
Ryu, Do Hyun [1 ,2 ]
Yun, Jaesook [1 ,2 ]
机构：
[1] Sungkyunkwan Univ, Dept Chem, Suwon 16419, South Korea
[2] Sungkyunkwan Univ, Inst Basic Sci, Suwon 16419, South Korea
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 09期
基金：
新加坡国家研究基金会;
关键词：
Copper; Dynamic kinetic resolution; Hydroboration; Kinetic resolution; Lactones; ASYMMETRIC TRANSFER HYDROGENATION; CONJUGATE REDUCTION; HYDROBORATION; KETONES;
D O I：
10.1002/adsc.202001353
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Kinetic resolution (KR) and dynamic kinetic resolution (DKR) of gamma-aryl and heteroaryl-substituted butenolides via CuH-catalyzed 1,4-hydroboration using pinacolborane is reported. With a copper-Ph-BPE catalyst, selectivity factors were extremely high (s=>400) with regard to the kinetic resolution of beta-methyl-gamma-phenyl butenolide; DKR was possible in the presence of an amine base (DBU), which facilitated racemization of the starting unsaturated lactones. The reaction provided easy access to highly enantioenriched gamma-butyrolactones (>99% ee) containing beta,gamma-substituents.
引用
收藏
页码：2377 / 2381
页数：5
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