A study on the synthesis of β-amino acids: the first synthesis of a bicyclic hemiaminal (3,3-dimethyl-1-(2,4,5-trifluorophenyl) tetrahydro-3H,5H-oxazolo[3,4-c] [1,3] oxazin-5-one)

  1. Ozlem GundogduORCID Logo,
  2. Ertan Sahin and
  3. Yunus KaraORCID Logo

Submitting author affiliation: Atatürk University, Erzurum, Turkey

Beilstein Arch. 2020, 202053. doi:10.3762/bxiv.2020.53.v1

Published 21 Apr 2020

  • Preprint

Abstract

We synthesized (4S)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5-(2,4,5-trifluorophenyl) oxazolidin-2-one and examined its Pd/C-catalyzed hydrogenation reaction. The condensation and rearrangement reaction of acetone with (4S)-4-(2-((tert-butyl dimethylsilyl)oxy)ethyl)-5-(2,4,5-trifluorophenyl)oxazolidin-2-one resulted in the formation of a hemiaminal structure containing a fused oxazine-oxazole ring, whose exact configuration was determined by X-ray crystal analysis. A mechanism was proposed to explain the formation of the fused oxazine-oxazole ring, which has a hemiaminal structure.

Keywords: Hemiaminal, cyclic urethane, vicinal amino-alcohol, oxazine ring, oxazole ring

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Gundogdu, O.; Sahin, E.; Kara, Y. Beilstein Arch. 2020, 202053. doi:10.3762/bxiv.2020.53.v1

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