Tetrahedron

Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 2.: Asymmetric synthesis of (1R, 2S)-2-fluorocyclopropylamine

T Akiba, O Tamura, M Hashimoto, Y Kobayashi…

Index: Akiba, Toshifumi; Tamura, Osamu; Hashimoto, Masaru; Kobayashi, Yuko; Katoh, Tadashi; et al. Tetrahedron, 1994 , vol. 50, # 13 p. 3905 - 3914

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Citation Number: 47

Abstract

The title synthesis was achieved by featuring diastereoface-selective cyclopropanation of (4R, 5S)-4, 5-diphenyl-3-vinyl-2-oxazolidinone and its related compounds, the chiral conformationally rigid N-vinylcarbamates, with zinc-monofluorocarbenoid, followed by hydrogenolysis of the major addition products. The diastereoface-selectivity of the cyclopropanation could be explained by the most stable conformation of 3-vinyl-2- ...