Premium
Catalytic Asymmetric Conjugate Addition of Mercaptans to β‐Substituted‐β‐Trifluoromethyl Oxazolidinone Enoates: Access to Chiral Trifluoromethylated Tertiary Thioethers and Thiols
Author(s) -
Chen Wenchao,
Jing Zhengzhong,
Chin Kek Foo,
Qiao Baokun,
Zhao Yan,
Yan Lin,
Tan ChoonHong,
Jiang Zhiyong
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201301027
Subject(s) - chemistry , stereocenter , trifluoromethyl , enantioselective synthesis , cinchona , conjugate , enantiomer , tertiary amine , catalysis , organic chemistry , organocatalysis , addition reaction , michael reaction , amine gas treating , combinatorial chemistry , medicinal chemistry , mathematical analysis , alkyl , mathematics
Abstract The first asymmetric conjugate addition of mercaptans to β‐substituted‐β‐trifluoromethyl oxazolidinone enoates has been developed. The opposite enantiomers of adducts, containing a trifluoromethylated hetero‐quaternary stereogenic centers, could be obtained by utilizing two pseudo‐enantiomeric Cinchona alkaloid‐derived tertiary amine/squaramides as catalysts. Potassium dihydrogen phosphate was found to accelerate the reaction rate without compromising the enantioselective excess. A variety of chiral trifluoromethylated tertiary thioethers and thiols were readily prepared with excellent enantioselectivity.