Highly diastereoselective nucleophilic addition of organometallic reagents to 2-pyrrolidinyl nitrones: a semiempirical approach |
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| Institution: | 1. Department of Chemistry, Kabi Nazrul College, Murarai, Birbhum 731 219, West Bengal, India;2. Faculty of Chemistry, University of Wroclaw, 14 F. Joliot-Curie, 50-383 Wroclaw, Poland;3. Departimento di Chimica, Parco Area delle Scienze 17/A, 43124 Parma, Italy;4. Department of Chemistry, Institute of Education (P.G.) for Women, Chandernagore, Hooghly, West Bengal 712138, India;1. Department of Medicinal Chemistry, Gilead Sciences Inc., 333 Lakeside Drive, Foster City, CA 94404, USA;2. Department of Biological Sciences, Gilead Sciences Inc., 7601 Dumbarton Cir, Fremont, CA 94555, USA;3. Department of Drug Metabolism, Gilead Sciences Inc., 333 Lakeside Drive, Foster City, CA 94404, USA;1. Université de Lille, F-59000 Lille, France;2. UDSL, EA 4481, UFR Pharmacie, F-59000 Lille, France;3. Instituto de Medecina Molecular, 1640-028, Lisbon, Portugal;4. Université Bordeaux, CNRS FRE3396, F-33000 Bordeaux, France;5. Inserm UMR-S1172, JPArc, F-59000 Lille, France;6. Inserm UMR 995, LIRIC, F-59000 Lille, France |
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| Abstract: | 2-Pyrrolidinyl nitrones 1 and 2 derived from l-proline and trans-4-hydroxy-l-proline, respectively, undergo nucleophilic additions of Grignard reagents and organolithium compounds with high syn selectivity, to yield enantiomerically pure pyrrolidinyl benzyl hydroxylamines. A rationale for the observed stereoselectivity based on semiempirical calculations is presented. |
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