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

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

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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 microwave; oxazolidin-2-ones; oxazolidine-2-thiones; thiazolidine-2-thiones
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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