Microwave-Assisted Improved Synthesis of Oxazolidin-2-ones, Oxazolidine-2-thiones and Thiazolidine-2-thione Chiral Auxiliaries

doi:10.3390/molecules16108803

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Molecules 2011, 16(10), 8803-8814; doi:10.3390/molecules16108803

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Microwave-Assisted Improved Synthesis of Oxazolidin-2-ones, Oxazolidine-2-thiones and Thiazolidine-2-thione Chiral Auxiliaries

Rosmarbel Morales-Nava, Mario Fernández-Zertuche * and Mario Ordóñez

Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Ave. Universidad 1001, Col. Chamilpa, Cuernavaca, Morelos, 62209, Mexico

* Author to whom correspondence should be addressed.

Received: 13 September 2011; in revised form: 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.

Keywords: microwave; oxazolidin-2-ones; oxazolidine-2-thiones; thiazolidine-2-thiones

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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.

AMA 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(10):8803-8814.

Chicago/Turabian Style

Morales-Nava, Rosmarbel; Fernández-Zertuche, Mario; Ordóñez, Mario. 2011. "Microwave-Assisted Improved Synthesis of Oxazolidin-2-ones, Oxazolidine-2-thiones and Thiazolidine-2-thione Chiral Auxiliaries." Molecules 16, no. 10: 8803-8814.

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