Copper-Catalyzed Enantioselective 1,2-Reduction of Cycloalkenones

被引：7

作者：

Shi, Yongjie ^{[1
,2
]}

Wang, Jingxin ^{[3
]}

Yin, Qin ^{[3
,4
]}

Zhang, Xumu ^{[3
]}

Chiu, Pauline ^{[1
,2
]}

机构：

[1] Univ Hong Kong, Dept Chem, Hong Kong, Peoples R China

[2] Univ Hong Kong, State Key Lab Synthet Chem, Hong Kong, Peoples R China

[3] Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China

[4] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518000, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 15期

关键词：

REDUCTIVE ALDOL CYCLIZATIONS; ASYMMETRIC HYDROGENATION; ALLYLIC ALCOHOLS; DIPHOSPHINE LIGANDS; REARRANGEMENT; DERIVATIVES; HYDRIDE; KETONES; SUBSTITUTION; ALDEHYDES;

D O I：

10.1021/acs.orglett.1c01744

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an asymmetric 1,2-reduction of cyclic alpha,beta-unsaturated ketones to access various enantiomerically enriched cyclic allylic alcohols under mild conditions, catalyzed by in situ generated copper hydride ligated with (R)-DTBM-C-3*-TunePhos. alpha-Brominated cydoalkenones were reduced with excellent enantioselectivities of up to 98% ee, while substrates that were without alpha-substituents were reduced chemoselectively, with moderate enantioselectivities.

引用

页码：5658 / 5663

页数：6

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