Enantioselective Cu-Catalyzed Nucleophilic Addition of Fluorinated Reagents: C-C Bond Formation for the Synthesis of Chiral Vicinal Difluorides

被引：17

作者：

Lin, Huaxin ^{[1
,2
]}

Jiao, Wei ^{[1
,2
]}

Chen, Zhiwei ^{[1
,2
]}

Han, Jian ^{[3
]}

Fang, Dongmei ^{[1
]}

Wang, Min ^{[1
,2
]}

Liao, Jian ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Sichuan Univ, Coll Chem Engn, Chengdu 610065, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 11期

关键词：

GEM-DIFLUOROALKENES; STEREOSELECTIVE-SYNTHESIS; ELEMENTAL FLUORINE; FUNCTIONALIZATION; DIFLUORINATION; SECONDARY; TERTIARY; ACIDS;

D O I：

10.1021/acs.orglett.2c00518

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we described the first enantioselective Cu/ sulfoxide phosphine (SOP) complex catalyzed nucleophilic addition of fluorinated enolates to gem-difluoroalkenes. The enantioenriched vicinal difluorides, containing a chiral tertiary fluoride and a fluoroalkene, were successfully afforded via C-C bond formation in good yields (up to 94% yield), high Z/E-selectivity (5:1 -> 50:1 for Zisomer), and excellent enantioselectivities (up to 98.5:1.5 er). Utility of this approach was demonstrated by modification of complex biologically active compounds.

引用

页码：2197 / 2202

页数：6

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