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Communication | Special issue | Vol 33, No. 2, 1992, pp.511-514
Published online, 1st January, 1970
DOI: 10.3987/COM-91-S74
Synthesis of 1-Alkyl-3-hydroxy-2-phenylazetidines

Takashi Toda,* Michinori Karikomi, Masabumi Ohshima, and Masaaki Yoshida

*Department of Applied Chemistry, Faculty of Engineering, Utsunomiya University, 7-1-2 Yoto, Utsunomiya 321-8585, Japan


Several (R *, S *)-1-alkyl-3-hydroxy-2-phenylazetidines (1) were synthesized by the reaction of (R *, R *)-2-(1-bromobenzyl)oxirane (2a) with aliphatic primary amines in good yields. By the reaction of (R *, S * )-2-(1-bromobenzyl)oxirane (2b), only (R *, R *)-2-aminomethyl-3-phenyloxirane (3) was obtained. Also, the reaction of (R *, R *)-2-(1-bromobenzyl)-2-methyloxirane (2c) gave a mixture of (R *, S *)-3-hydroxy-3-methyl-2-phenylazetidine (4) as the major product and (R *, S *)-2-aminomethyl-2-methyl-3-phenyloxirane (5) as the minor product.