Synthesis and stereoselective oxidation of α-thio-β-chloropropenyloxazolidin-2-ones |
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| Authors: | Marie Kissane Maureen Murphy Simon E Lawrence Anita R Maguire |
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| Institution: | 1. Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland;2. Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland |
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| Abstract: | The 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 shows modest diastereocontrol. However, via a combination of diastereoselective oxidation and subsequent kinetic resolution in the sulfoxide oxidation, diastereoselectivities of up to 94% de have been achieved. |
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