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Paper | Special issue | Vol 44, No. 1, 1997, pp.227-236
Published online, 1st January, 1970
DOI: 10.3987/COM-96-S12
Synthesis of Indolizidine Derivatives Trifluoromethylated at Bridgehead Position via Acyl Iminium Ion Intermediates Derived from Ring-Chain Tautomerism of 5,5,5-Trifluoro-4-oxopentanoyl Arylethylamides

Takashi Okano, Tsutomu Sakaida, and Shoji Eguchi*

*Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


Acyliminium ion intermediates were generated from the stable cyclic form of 5,5,5-trifluoro- 4- oxopentanoyl arylethylamides via acid catalyzed dehydration. Electrophilic cyclization of aryl group led to fused indolizidinones.