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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When a peer-reviewed version of this preprint is available in the Beilstein Journals, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:
Gundogdu, O.; Sahin, E.; Kara, Y. Beilstein Arch. 2020, 202053. doi:10.3762/bxiv.2020.53.v1
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