4.7 Article

Enantioselective Vinylogous Mannich-Type Reactions to Construct CF3S-Containing Stereocenters Catalysed by Chiral Quaternary Phosphonium Salts

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 9, Pages 1851-1857

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901621

Keywords

trifluoromethylthio-containing building blocks; a nitro group; enantioselectivities; vinylogous Mannich-type reactions; chiral quaternary phosphonium salts

Funding

  1. National Natural Science Foundation of China [21272247, 21572247, 21871282]
  2. Chinese Academy of Sciences [XDB 20020100]
  3. Shanghai Sailing Program [C81YF19S001]
  4. Gaoyuan Discipline of Shanghai-Environmental Science and Engineering (Resource Recycling Science and Engineering)

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A series of benzyl trifluoromethyl sulphides bearing a nitro group were utilized as CF3S-containing building blocks to construct chiral CF3S-containing molecules via enantioselective vinylogous Mannich-type reactions. In such reactions, high yields and enantioselectivities were obtained using chiral quaternary phosphonium salts derived from amino acids. Moreover, a chiral cyclic urea bearing the CF3S moiety was obtained from further transformation of the product.

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