A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones |
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| Institution: | 1. Department of Medical Genetics, School of Medicine, Iran University of Medical Sciences (IUMS), Tehran, Iran;2. Rajaie Cardiovascular Medical and Research Center, Iran University of Medical Sciences, Tehran, Iran;3. Department of Laboratory Sciences, School of Allied Medical Sciences, Zahedan University of Medical Sciences, Zahedan, Iran;1. Department of Physics and Astronomy, Wayne State University, Detroit, MI 48201, USA;2. Chemistry Division, Bhabha Atomic Research Centre, Mumbai 400085, India;3. Department of Natural Sciences, University of Michigan, Dearborn, MI 48128, USA |
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| Abstract: | A novel highly stereoselective synthesis of chiral mono- and bicyclic 4- and 4,5-substituted 2-oxazolidinones starting from β-keto esters was developed. After bioreduction with S. cerevisiae the resulting homochiral β-hydroxy esters are transformed into their hydrazides. Treatment with NaNO2/H+ then furnishes 2-oxazolidinones in high e.e. (∼99%) and d.e. (>99%). The ring formation proceeds via a highly concerted sextet rearrangement with full retention of configuration at the stereocentres. Enantiopure 1,2-amino alcohols can subsequently be obtained by saponification of the 2-oxazolidinone products. |
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