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Synthesis 2011(22): 3627-3634  
DOI: 10.1055/s-0030-1260239
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Addition-Intramolecular N-Cyclization of Carbamates Mediated by Alkali Metallic Reagents as an Approach to 4-(Fluoroalkyl)oxazolidin-2-ones

Xue-Yan Yanga, Xiang Fang*a, Zheng-Hua Jua, Yun-Li Hua, Fan-Hong Wu*a,b
a Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
Fax: +86(21)64253074; e-Mail: fangxiang@ecust.edu.cn; e-Mail: wfh@ecust.edu.cn;
b School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 200235, P. R. of China
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Publication History

Received 23 July 2011
Publication Date:
26 September 2011 (online)

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Abstract

A mild and straightforward strategy for the synthesis of 4-(fluoroalkyl)oxazolidin-2-ones via one-pot addition-intramolecular N-cyclization of allyl carbamates with fluoroalkyl iodides is presented. The reaction proceeded in moderate to good yield through regiocontrol and an increase in the reactivity of the ambident nucleophiles by the use of alkali metallic reagents.

Key words

allyl carbamates - 4-(fluoroalkyl)oxazolidin-2-ones - addition-intramolecular N-cyclization - alkali metallic reagents

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