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Paper | Special issue | Vol 40, No. 2, 1995, pp.753-756
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S63
Cyclization of the Ene Reaction Products from Hexafluoroacetone Imine: Synthesis of Bis(trifluoromethyl)pyrrolidine Derivatives

Tetsuo Shimada, Akihiro Fujimoto, Toshiyuki Takagi, Mayumi Koyama, Akira Ando, and Itsumaro Kumadaki

*Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata-shi, Osaka 573-0101, Japan

Abstract

N-Tosylhexafluoroacetone imine reacted as a good enophile with ene components to give α,α-bis(trifluoromethyl)homoalIylamine derivatives. Cyclization of the ene reaction products in the presence of p-toluenesulfonic acid gave α,α-bis(trifluoromethyl)pyrrolidine derivatives, when the δ position of the homoallylamino group was substituted with an aromatic ring, while no reaction occurred, when substituted with an alkyl group.