Molecules 2011, 16(10), 8803-8814; doi:10.3390/molecules16108803
Microwave-Assisted Improved Synthesis of Oxazolidin-2-ones, Oxazolidine-2-thiones and Thiazolidine-2-thione Chiral Auxiliaries
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Ave. Universidad 1001, Col. Chamilpa, Cuernavaca, Morelos, 62209, Mexico
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Received: 13 September 2011 / Revised: 7 October 2011 / Accepted: 18 October 2011 / Published: 20 October 2011
(This article belongs to the Special Issue Microwave Assisted Synthesis)
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Abstract
A microwave assisted method for the synthesis of some typical 4-substituted oxazolidinone chiral auxiliaries used in asymmetric synthesis is reported in this work. Under these conditions, treatment of (S)-phenylalaninol, (S)-phenylglycinol, (S)-valinol and (1S, 2R)-norephedrine with ethyl carbonate or carbon disulfide under the appropriate and specific microwave reaction conditions, led to an efficient synthesis of some oxazolidin-2-ones, oxazolidine-2-thiones and thiazolidine-2-thiones. The methodology reported in this paper provides these chiral auxiliaries with improved yields and a remarkable reduction on the reaction times, particularly in the case of thiazolidine-2-thiones, as compared with the conventional methods. All the auxiliaries prepared here show spectroscopic data in full agreement with those previously reported in the literature.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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MDPI and ACS Style
Morales-Nava, R.; Fernández-Zertuche, M.; Ordóñez, M. Microwave-Assisted Improved Synthesis of Oxazolidin-2-ones, Oxazolidine-2-thiones and Thiazolidine-2-thione Chiral Auxiliaries. Molecules 2011, 16, 8803-8814.
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