Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide

被引：168

作者：

Liu, Xiang ^{[1
,2
]}

An, Rui ^{[1
,2
]}

Zhang, Xuelin ^{[1
,2
]}

Luo, Jie ^{[1
,2
]}

Zhao, Xiaodan ^{[1
,2
]}

机构：

[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Inst Organ Chem, Guangzhou 510275, Guangdong, Peoples R China

[2] Sun Yat Sen Univ, Sch Chem & Chem Engn, MOE Key Lab Bioinorgan & Synthet Chem, Guangzhou 510275, Guangdong, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 19期

关键词：

alkenes; asymmetric catalysis; chiral sulfides; organocatalysis; trifluoromethylthiolation; HYPERVALENT IODONIUM YLIDE; ALPHA-FLUORINATED ETHERS; C-H BONDS; MEDICINAL CHEMISTRY; BORONIC ACIDS; ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION; OXIDATIVE TRIFLUOROMETHYLTHIOLATION; SILVER(I) TRIFLUOROMETHANETHIOLATE; INTRAMOLECULAR CARBOSULFENYLATION; UNACTIVATED ALKENES;

D O I：

10.1002/anie.201601713

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane-based bifunctional chiral sulfide catalyst and a shelf-stable electrophilic SCF3 reagent. The desired products were formed with diastereoselectivities of >99:1 and good to excellent enantioselectivities. The transformation represents the first enantioselective trifluoromethylthiolation of alkenes and the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center.

引用

页码：5846 / 5850

页数：5

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