Highly stereoselective synthesis of C2-chiral and meso nitroxides from an optically active pyrrolidine |
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| Affiliation: | 1. Research Institute of Chemistry and Geology, Oles Honchar Dnipro National University, 72 Gagarina Ave., Dnipro 49010, Ukraine;2. Department of Chemistry and Biochemistry, University of Texas at Dallas, 800 West Campbell Road, Richardson, TX 75080, United States;3. SSI «Institute for Single Crystals», National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61001, Ukraine;1. Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering and High Technology Research Center, Kansai University, Suita, Osaka 564-8680, Japan;2. Graduate School of Human and Environmental Studies, Kyoto Univesity, Kyoto 606-8501, Japan;1. Icahn School of Medicine at Mount Sinai, Division of Infectious Diseases, New York, NY, USA;2. Icahn School of Medicine at Mount Sinai, Tisch Cancer Institute, New York, NY, USA;3. AIDS and Cancer Virus Program Inc., Frederick, MD, USA;4. Oncovir Inc., Washington, DC, USA |
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| Abstract: | Starting from (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine 1, hydroxylamine cis-3 was synthesized with high stereoselectivity by successive oxidation and addition of PhMgBr. By using PhLi, trans (C2-chiral) pyrrolidine nitroxide trans-7 was obtained from nitrone 5 derived from hydroxylamine 3. The cis (meso) counterpart cis-7 was produced along with trans-7 when PhMgBr was employed in place of PhLi. Moreover, cis-7 was also obtained selectively by using PhLi and Et2AlCl with nitrone 5. The change of stereochemical bias observed when EtMgBr and/or nitrone 10 bearing an ethyl group were employed is also discussed. |
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