Journal
TETRAHEDRON
Volume 67, Issue 1, Pages 69-74Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.11.032
Keywords
Ruppert-Prakash reagent; Nucleophilic trifluoromethylation; Cyclic imines; alpha-trifluoromethylated alkaloids
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Funding
- Deutsche Forschungsgemeinschaft [RO 362/42/1]
- RFBR [10-03-91333-NNIO_a]
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We have demonstrated that the Ruppert-Prakash reagent is able to react with a number of cyclic imines under acidic condition to afford the corresponding alpha-trifluoromethyl derivatives of nitrogen heterocycles. 5-7-Membered cyclic imines bearing various alkyl, aryl or heterocyclic group were successfully involved in this transformation. Novel trifluoromethylated analogues of nicotine, anabasine, and homoanabasine alkaloids were synthesized. (C) 2010 Elsevier Ltd. All rights reserved.
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