Catalytic,asymmetric aza-Baylis–Hillman reaction of N-sulfonated imines with 2-cyclohexen-1-one and 2-cyclopenten-1-one in the presence of a chiral phosphine Lewis base |
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| Institution: | 1. Guizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, College of Pharmacy, Guizhou University, Guiyang 550025, China;2. Key Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany;2. Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia;1. Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700 054, India;2. Bose Institute, Department of Biophysics, P-1/12, C.I.T. Scheme VII-M, Kolkata 700 054, India;1. NMR-based Structural Biology, Max-Planck-Institute of Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany;2. Pharmaceutical Chemistry, Friedrich-Schiller Universität, Philosophenweg 14, 07743 Jena, Germany |
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| Abstract: | In the aza-Baylis–Hillman reaction of N-sulfonated imines with 2-cyclohexen-1-one or 2-cyclopenten-1-one, we found that by using (R)-2′-dimethylphosphanyl-1,1′]binaphthalenyl-2-ol LB1 as a chiral phosphine Lewis base, the corresponding Baylis–Hillman adducts 2 or 3 can be obtained in good yields and moderate enantiomeric excess. The structure of this chiral phosphine Lewis base on chiral induction in this reaction has also been discussed. |
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