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Synlett 2009(19): 3155-3158  
DOI: 10.1055/s-0029-1218284
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Syntheses of N-Aryloxazolidin-2-ones via Tandem Reactions of Vinyl Sulfonium Salts

Chunsong Xie, Deyu Han, Jinhua Liu*, Tian Xie*
Center for Biomedicine and Health, Hangzhou Normal University, Hangzhou 310012, P. R. of China
Fax: +86(571)28865630; e-Mail: ljh@hznu.edu.cn;
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Publication History

Received 30 July 2009
Publication Date:
09 October 2009 (online)

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Abstract

An unprecedented and efficient domino reaction of diphenyl vinyl sulfonium salt with carbamates leading to the syntheses of N-aryloxazolidin-2-ones has been developed. The scope of this transformation has been studied and a plausible mechanism has been proposed.

Key words

N-aryloxazolidin-2-one - tandem reaction - vinyl sulfonium - carbamate

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14

Typical Procedure for the Tandem Reactions - Synthesis of 3-Phenyloxazolidin-2-one
tert-Butyl phenylcarbamate (96 mg, 0.5 mmol) and Et3N (152 mg, 1.5 mmol) were charged into an oven-dried flask, followed by the addition of CH2Cl2 (2 mL) under the protection of nitrogen atmosphere to form a solution. The solution of diphenyl vinyl sulfonium triflate (543 mg, 1.5 mmol) in CH2Cl2 (3 mL) was added into the above solution by syringe under N2 at r.t. The reaction mixture was then put into a 45 ˚C oil bath to react for 24 h. After the completion of reaction, the solvent was removed under reduced pressure. The residue was then separated on a silica gel column by using PE-EtOAc (1:2) as eluent, and the final product was obtained as pale yellow powder (42 mg, 52%). ¹H NMR (400 MHz, CDCl3, TMS): δ = 7.51 (d, J = 8.0 Hz, 2 H), 7.36 (t, J = 8.0 Hz, 2 H), 7.12 (t, J = 7.4 Hz, 1 H), 4.42 (t, J = 8.0 Hz, 2 H), 3.99 (t, J = 8.0 Hz, 2 H). ¹³C NMR (100 MHz, CDCl3): δ = 155.3, 138.3, 129.1, 124.1, 118.2, 61.3, 45.2. HRMS (EI): m/z calcd for C9H9NO2 [M]+: 163.0633; found: 163.0627.