Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide

被引：166
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
收藏
页码：5846 / 5850
页数：5
相关论文
共 88 条
[1]  
Alazet S., 2013, ANGEW CHEM, V125, P11014, DOI DOI 10.1002/ANGE.201305179
[2]   Electrophilic Trifluoromethylthiolation of Carbonyl Compounds [J].
Alazet, Sebastien ;
Zimmer, Luc ;
Billard, Thierry .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (28) :8589-8593
[3]   Base-Catalyzed Electrophilic Trifluoromethylthiolation of Terminal Alkynes [J].
Alazet, Sebastien ;
Zimmer, Luc ;
Billard, Thierry .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (41) :10814-10817
[4]  
[Anonymous], 2013, Angew. Chem, DOI [10.1002/ange.201209817, DOI 10.1002/ANGE.201209817]
[5]  
[Anonymous], 2011, Angew. Chem., DOI [10.1002/ange.201102543, DOI 10.1002/ANGE.201102543]
[6]  
[Anonymous], 2013, ANGEW CHEM, DOI DOI 10.1002/ANGE.201301438
[7]  
[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANGE.201205156
[8]  
[Anonymous], 2009, ANGEW CHEM
[9]  
[Anonymous], 2013, ANGEW CHEM, DOI [10.1002/ange.201208432, DOI 10.1002/ANGE.201208432]
[10]   Trifluoromethylthiolation of Allylsilanes and Silyl Enol Ethers with Trifluoromethanesulfonyl Hypervalent Iodonium Ylide under Copper Catalysis [J].
Arimori, Sadayuki ;
Takada, Masahiro ;
Shibata, Norio .
ORGANIC LETTERS, 2015, 17 (05) :1063-1065
123456789