Ready access to enantiopure 5-substituted-3-pyrrolin-2-ones from N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone (BIGN) |
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| Institution: | 1. Department of Psychology and Neuroscience, Center for Neuroscience, University of Colorado Boulder, Boulder, CO 80309, USA;2. University of Texas at Austin, Division of Pharmacology and Toxicology, Austin, TX 78712, USA;1. Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15771, Greece;2. Division of Immunology, Biomedical Sciences Research Center “Alexander Fleming”, Athens 16672, Greece;3. NovaMechanics Ltd, Nicosia 1065, Cyprus |
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| Abstract: | The reaction of the lithiated salt of methyl propiolate with N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone (BIGN) afforded the corresponding propargyl hydroxylamines in a stereocontrolled way depending on the nature of the Lewis acid used as an additive. Subsequent reduction of the obtained hydroxylamines provided chiral 5-substituted-3-pyrrolin-2-ones, in high overall yields. |
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