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      Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates : access to chiral trifluoromethylated tertiary thioethers and thiols

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      Author
      Chen, Wenchao
      Jing, Zhengzhong
      Chin, Kek Foo
      Qiao, Baokun
      Zhao, Yan
      Yan, Lin
      Tan, Choon-Hong
      Jiang, Zhiyong
      Date of Issue
      2014
      School
      School of Physical and Mathematical Sciences
      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.
      Subject
      DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
      Type
      Journal Article
      Series/Journal Title
      Advanced synthesis & catalysis
      Rights
      © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
      Collections
      • SPMS Journal Articles
      http://dx.doi.org/10.1002/adsc.201301027
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