The reaction of cyclic imines with the Ruppert-Prakash reagent. Facile approach to alpha-trifluoromethylated nornicotine, anabazine, and homoanabazine

作者：Shevchenko Nikolay E; Vlasov Katja; Nenajdenko Valentine G^*; Roeschenthaler Gerd Volker

来源：Tetrahedron, 2011, 67(1): 69-74.

DOI：10.1016/j.tet.2010.11.032

• Ruppert-Prakash reagent
• Nucleophilic trifluoromethylation
• Cyclic imines
• alpha-trifluoromethylated alkaloids

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.

• 出版日期2011-1-7