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Paper | Special issue | Vol 76, No. 2, 2008, pp.1155-1170
Published online, 22nd May, 2008
DOI: 10.3987/COM-08-S(N)74
Epimerization of trans-3-Arylaziridine-2-carboxylates at the C3 Position

Takuya Kumamoto,* Shin-ichiro Nagayama, Yukiko Hayashi, Hiroaki Kojima, Lemin David, Waka Nakanishi, and Tsutomu Ishikawa

*Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho Inage-ku, Chiba 263-8522 Japan

Abstract

We describe here effective epimerization of trans to cis isomer of 1-benzyl-3-arylaziridine-2-carboxylates. The combination of samarium metal, iodine and N,N-dimethylaminoethanol promoted the epimerization of trans isomer to a ca. 1 : 1 mixture of cis and trans ones. Investigating more effective catalyst, indium chloride was found to afford a ca. 2 : 1 mixture of cis and trans isomers. Epimerization at benzylic position in the aziridines is suggested from the result with optically active ones. Preparation of cis-2-indolylaziridine towards construction of aziridinomitosene skeleton was achieved in this epimerization reaction.