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■ Selective Formation of 1-Azetine Derivatives via 1,3-Photoacyl Migration of Substituted α-Dehydrophenylalanines

Kanji Kubo,* Masaomi Koshiba, Hideki Hoshina, and Tadamitsu Sakurai*

*Departmnet of Applied Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

Irradiation of (Z)-N-substituted benzoyl-α-dehydrophenylalanines in methanol with Pyrex-filtered light was found to selectively give 1-azetine derivatives, which may be derived from 1,3-acyl migration of the excited-state (E)-isomer, whereas no 1,5-acyl shift of the (Z)-isomer occurred owing to the stereoelectronic effects of the bulky aromatic acyl substituent.