Tetrahedron

Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R, 2S)-2-fluorocyclopropylamine by the use of …

…, T Katoh, K Nakatani, M Kamada, I Hayakawa, T Akiba…

Index: Tamura, Osamu; Hashimoto, Masaru; Kobayashi, Yuko; Katoh, Tadashi; Nakatani, Kazuhiko; Kamada, Masahiro; Hayakawa, Isao; Akiba, Toshifumi; Terashima, Shiro Tetrahedron, 1994 , vol. 50, # 13 p. 3889 - 3904

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Citation Number: 43

Abstract

The title synthesis was achieved by employing highly cis-selective cyclopropanation of N- benzyl-N-vinylcarbamates with zinc-monofluorocarbenoid, deprotection of the formed N- benzyl-N-(cis-2-fluorocyclopropyl) carbamates, and optical resolution of the resulting dl-cis-2- fluorocyclopropylamine by the use of l-menthyl chloroformate as a resolving agent. The cis- selectivity observed for the key cyclopropanation could be explained by the bent transition ...