Synthesis of chiral sultams and their application as chiral auxiliaries in an asymmetric Diels–Alder reaction |
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| Affiliation: | 1. Department of Chemistry, Xiamen University, Xiamen, China;2. Department of Chemistry and Central Laboratory of the Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong;1. Influenza Research Institute, St. Petersburg, Russia;2. Southern Federal University, Rostov-on-Don, Russia;1. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing Key Laboratory of Environmental Science and Engineering, Beijing 100081, China;2. National Development Center of High Technology Green Materials, Beijing 100081, China;3. State Key Laboratory of Chemical Resource Engineering, Beijing Key Laboratory of Electrochemical Process and Technology for Materials, Beijing University of Chemical Technology, Beijing 100029, China;1. Department of Pharmaceutical Analysis and Nuclear Pharmacy, Faculty of Pharmacy, Comenius University in Bratislava, Odbojarov 10, 832 32 Bratislava, Slovakia;2. Department of NMR Spectroscopy and Mass Spectrometry, Faculty of Chemical and Food Technology, Slovak University of Technology, 812 37 Bratislava, Slovakia;3. Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojarov 10, 832 32 Bratislava, Slovakia;4. Department of Organic Chemistry, Jagiellonian University, 30 060 Kraków, Poland |
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| Abstract: | A number of bicyclic chiral sultams were synthesized based on 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrones with prop-1-ene-1,3-sultone. The corresponding N-enoyl sultams were prepared by acylation. Their relative effectiveness as new chiral auxiliaries in asymmetric synthesis was evaluated for the asymmetric Diels–Alder reactions with cyclopentadiene. Good chemical yield and excellent endo selectivity were observed. The relationship between the structure and their effectiveness in promoting asymmetric induction of the synthetic chiral sultams was investigated. |
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