Elsevier

Tetrahedron Letters

Volume 54, Issue 35, 28 August 2013, Pages 4717-4720
Tetrahedron Letters

Dehydrative synthesis of chiral oxazolidinones catalyzed by alkali metal carbonates under low pressure of CO2

https://doi.org/10.1016/j.tetlet.2013.06.100Get rights and content

Abstract

Dehydrative synthesis of oxazolidinones from amino alcohols and CO2 was achieved in the presence of alkali metal carbonates such as Cs2CO3 as catalyst. It is noteworthy that 1 atm of CO2 is enough for the reaction to proceed and no special dehydrating agent is required in this system. A mechanstic study showed that the OH of amino alcohol acts as nucleophile and the OH in the carbamic acid moiety is liberated during the cyclization process.

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Acknowledgments

This work was supported by funds from Asahi Glass, Asahi Kasei Chemicals, Kuraray, Mitsubishi Chemical, Mitsui Chemicals, Nissan Chemical Ind., and Sumitomo Chemical, Asahi Glass Foundation and ACT-C, JST. S.W.F. and Y.T. were financially supported by the GCOE in chemistry, Nagoya University (NU) and IGER in chemistry, NU. The authors wish to thank Professor R. Noyori (NU & RIKEN) for fruitful discussions and Professor P. Butko (NU) for technical advice.

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