Stereoselective synthesis of 3-alkylsulfinylmethylisoxazolines and their use as chiral nucleophiles in the chain elongation of 2,3-O-isopropylidene-d-glyceraldehyde |
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| Institution: | 1. School of Mechanical Engineering, University of Science and Technology Beijing, Beijing, 100083, China;2. School of Engineering and Applied Science, Aston University, Birmingham B4 7ET, UK |
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| Abstract: | The reaction of racemic 3-methylisoxazolines and enantiomerically pure (RS)- and (SS)-methanesulfinates and (RS)- and (SS)-ethanesulfinates of 1,2:5,6-di-O-isopropylidene-d-glucofuranose allows enantiomerically pure 3-alkylsulfinylmethylisoxazolines with both absolute configurations at sulfur to be obtained. One of these has been used as a chiral nucleophile in the four carbon homologation of 2,3-O-isopropylidene-d-glyceraldehyde 17. |
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