Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion |
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| Institution: | 1. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi 330013, PR China;2. Department of Chemistry, Nanchang University, Nanchang, Jiangxi 330031, PR China;1. Chemistry Department, College of Science, University of Anbar, Ramadi, Iraq;2. Raman Research Institute, Soft Condensed Matter Group, Sadashivanagara, Bengaluru 560080, Karnataka, India;3. Department of Chemistry, Central College Campus, Bangalore University, Bengaluru 560001, Karnataka, India;4. Liquid Crystal Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia;1. Department of Chemistry, Bard College, 30 Campus Road, Annandale-on-Hudson, NY 12504, United States;2. Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, United States;1. Department of Chemistry, Faculty of Science and Arts, Ordu University, Ordu, Turkey;2. Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, Samsun, Turkey;3. Central Research Laboratory, Eskişehir Osmangazi University, Eskisehir, Turkey;4. Department of Physics, Science Faculty, Anadolu University, Eskisehir, Turkey;1. Institute of Chemistry, University of Bialystok, Piłsudskiego 11/4, 15-443 Białystok, Poland;2. Institute of Organic Chemistry, Polish Academy of Science, Kasprzaka 44, 01-224 Warsaw, Poland |
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| Abstract: | A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (−)-indolizidine 195B, (−)-indolizidine 223AB, (+)-monomorine and (−)-3-butyl-5-propyl indolizidine. |
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