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

Full Text: HTML

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- ...

Related Articles:

Isocyanates, part 5 Synthesis of chiral oxazolidin-2-ones and imidazolidin-2-ones via DMAP-catalyzed isocyanation of amines with di-tert-butyl dicarbonate

[Knoelker, Hans-Joachim; Braxmeier, Tobias Tetrahedron Letters, 1998 , vol. 39, # 51 p. 9407 - 9410]

Resolution of pentafluorophenyl esters using oxazolidin-2-ones

[Tetrahedron Letters, , vol. 51, # 45 p. 5892 - 5895]

Bis (O-nitrophenyl) Carbonate as a New Reagent for the Synthesis of Chiral Oxazolidin-2-ones

[Simon, Monika; Micle, Andreea; Badea, Valentin; Csunderlik, Carol Synthetic Communications, 2009 , vol. 39, # 15 p. 2633 - 2639]

Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans

[Analytical Chemistry, , vol. 81, # 24 p. 10215 - 10226]

Facile inversion of configuration of N-Boc-β-aminoalcohols via SN 2 cyclization to oxazolidinones

[Tetrahedron Letters, , vol. 41, # 51 p. 10071 - 10074]

More Articles...