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Communication | Regular issue | Vol 9, No. 4, 1978, pp.473-480
Published online, 1st January, 1970
DOI: 10.3987/R-1978-04-0473
Sterically Controlled Synthesis of cis-1-Benzyl-2-methoxycarbonyl-3-phenylaziridine

Isao Nakamura and Kaoru Harada*

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


The treatment of methyl erythro-2,3-dibromo-3-phenylpropionate (I), methyl cis- and trans-α-bromocinnamate (IIa, IIb) with benzylamine resulted in the formation of the same sole product cis-1-benzyl-2-methoxycarbonyl-3-phenylaziridine (III). A plausible stereochemical pathway was discussed. The compound III was converted to phenylalanine (V) by hydrogenation and threo-β-phenylserine (VI) by hydration reaction.