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■ A New Approach to 5-Arylpyrrolidin-2-ones via 5-endo-Trig Radical Cyclization of α-Halo- or α-Thio-substituted N-(1-Arylethenyl)acetamides

Tatsunori Sato, Naomi Machigashira, Hiroyuki Iahibashi, and Masazumi Ikeda*

*Kyoto Pharmaceutical University, Misasagi-Shichonocho, Yamashina, Kyorto 607-8414, Japan

Abstract

N-(1-Phenylethenyl)carbamoylmethyl radicals generated by tributyltin hydride-mediated cleavage of carbon-halogen or carbon-sulfur bond underwent smooth cyclization in a “disfavored” 5-endo-trig manner to give 5-phenylpyrrolidin-2-one. This method was applied to the synthesis of (±)-cotinine.