Tetrahedron letters

Synthesis and optical resolution of dl-cis-2-fluorocycloproplylamine, the key component of the new generation of quinolonecarboxylic acid, DU-6859

…, M Hashimoto, Y Kobayashi, T Katoh, K Nakatani…

Index: Tamura; Hashimoto; Kobayashi; Katoh; Nakatani; Kamada; Hayakawa; Akiba; Terashima Tetrahedron Letters, 1992 , vol. 33, # 24 p. 3483 - 3486

Full Text: HTML

Citation Number: 32

Abstract

Abstract The title synthesis was accomplished by featuring highly cis-selective cyclpropanation of an N-vinylcarbamate with zinc-monofluorocarbenoid followed by deprotection of the formed N-(cis-2-fluorocyclopropyl) carbamate. Optical resolution of dl-cis- 2-fluorocyclopropylamine was also achieved by employing l-menthyl chloroformate as a resolving agent.

~83%

~53%

Synthetic studies on the key component of the new generation...

[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]