Synthesis and stereoselective oxidation of α-Thio-β- chloropropenyloxazolidin-2-ones

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Synthesis and stereoselective oxidation of α-Thio-β- chloropropenyloxazolidin-2-ones

Kissane, Marie; Murphy, Maureen; Lawrence, Simon E.; Maguire, Anita R.
Date: 2010-11-08
Copyright: © 2010 Elsevier Ltd. NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron: Asymmetry. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron: Asymmetry, [21, 20, (08/11/2010)] DOI: 10.1016/j.tetasy.2010.10.007
Citation: KISSANE, M., MURPHY, M., LAWRENCE, S. E. & MAGUIRE, A. R. 2010. Synthesis and stereoselective oxidation of α-thio-β-chloropropenyloxazolidin-2-ones. Tetrahedron: Asymmetry, 21, 2550-2558. doi: 10.1016/j.tetasy.2010.10.007
Published Version: 10.1016/j.tetasy.2010.10.007

Abstract:

Investigation of the stereoselective reaction of α-thiopropanoyloxazolidin-2-ones with NCS to yield α-thio-β-chloropropenyloxazolidin-2-ones is described. Diastereoselective sulfur oxidation of the resulting α-thio-β-chloropropenyloxazolidin-2-ones is also discussed, with modest diastereocontrol achieved. However, through a combination of diastereoselective oxidation and subsequent kinetic resolution in the sulfoxide oxidation, diastereoselectivities of up to 94% de are achieved.

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