Copper-Catalyzed Enantioselective Hydroboration of 1,1-Disubstituted Alkenes: Method Development, Applications and Mechanistic Studies

被引：12

作者：

Wen, Lu ^{[1
]}

Cheng, Fengchang ^{[1
]}

Li, Han ^{[2
]}

Zhang, Shuoqing ^{[2
]}

Hong, Xin ^{[2
]}

Meng, Fanke ^{[1
]}

机构：

[1] Chinese Acad Sci, State Key Lab Organomet Chem, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

[2] Zhejiang Univ, Dept Chem, 38 Zheda Rd, Hangzhou 310027, Zhejiang, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 01期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; copper; copper-boron addition; hydroboration; organoboron compounds; ASYMMETRIC HYDROBORATION; ARYL ALKENES; CARBOXYLIC-ACIDS; BORYL COMPLEXES; CUH; VINYLARENES; DESYMMETRIZATION; NUCLEOPHILES; ARYLBORATION; SEQUENCE;

D O I：

10.1002/ajoc.201700503

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu-catalyzed enantioselective Cu-B(pin) addition to 1,1-disubstituted alkenes generating tertiary alkylcopper complexes that contain a quaternary stereogenic center, followed by the protonation of the complexes are presented. The resulting formal hydroboration products are formed in up to 98% yield and 99:1 enantiomeric ratio. The C-B(pin) moiety can be converted to a variety of useful functional groups. The method is applied to the enantioselective formal synthesis of (R)-ketoprofen. Detailed stereochemical models for enantioselective induction were elucidated through DFT calculations.

引用

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页码：103 / 106

页数：4

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