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Keywords:

  • Alcohols, β-amino-α-(trifluoromethyl);
  • Aziridines, 2-(trifluoromethyl)-;
  • 1,3-Oxazolidines, 5-(trifluoromethyl)-;
  • 1,3,2-Oxazaphospholidines, 5-(trifluoromethyl)-;
  • 1,2,3-Oxathiazolidines, 5-(trifluoromethyl)-;
  • Trifluoromethyl heterocycles;
  • X-Ray crystallography

Abstract

Nucleophilic trifluoromethylation of α-imino ketones 2, derived from arylglyoxal, with RuppertPrakash reagent (CF3SiMe3) offers a convenient access to the corresponding O-silylated β-imino-α-(trifluoromethyl) alcohols. In a ‘one-pot’ procedure, by treatment with NaBH4, these products smoothly undergo reduction and desilylation yielding the expected β-amino-α-(trifluoromethyl) alcohols 4. The latter were used as starting materials for the synthesis of diverse trifluoromethylated heterocycles, including aziridines 5, 1,3-oxazolidines 8, 1,3-oxazolidin-2-ones 9, 1,3,2-oxazaphospholidine 2-oxides 10, 1,2,3-oxathiazolidine 2-oxides 11, and morpholine-2,3-diones 12. An optically active 5-(trifluoromethyl)-substituted 1,3-oxazolidin-2-one 9g was also obtained.