Asymmetric synthesis of (4S,5S)-2-oxo-4-phenyloxazolidine-5-carboxylic acid using a 1,2-addition of PhMgBr to an N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA |
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| Authors: | K. Chandra Babu Raman Vysabhattar K.S.V. Srinivas Satish Nigam G. Madhusudhan K. Mukkanti |
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| Affiliation: | 1. Inogent Laboratories Private Limited, A GVK BIO Company, Nacharam, Hyderabad 500 076, India;2. Centre for Pharmaceutical Sciences, J.N.T. University, Kukatpally, Hyderabad 500 072, India |
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| Abstract: | We report an asymmetric synthesis of (4S,5S)-2-oxo-4-phenyloxazolidine-5-carboxylic acid via stereoselective addition of phenylmagnesium bromide (PhMgBr) to an N-sulfinimine derived from (R)-glyceraldehyde acetonide. (S)- and (R)-Glyceraldehyde acetonides, important chiral synthons in synthetic organic chemistry, are prepared from the corresponding epichlorohydrin using an identical synthetic methodology. |
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