A new approach to enantioselective cyanation of imines with Et2AlCN |
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| Institution: | 1. School of Pharmaceutical Sciences of Zhengzhou University and Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, No. 100, KeXue DaDao, Zhengzhou 450001, PR China;2. College of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, PR China;1. Institute of Chemical Technology, Faculty of Food and Biochemical Technology, Department of Chemistry of Natural Compounds, Technická 5, 16628 Prague 6, Czech Republic;2. Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 16610 Prague 6, Czech Republic;1. Biochemistry and Molecular Biology Research Platform, College of Life Science, Northwest A&F University, Yangling, Shaanxi 712100, China;2. Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi 712100, China;1. School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, PR China;2. School of Pharmacy, Taizhou Polytechnic College, Taizhou 225300, PR China;1. 1st Department of Medicine, University of Szeged, Korányi fasor 8-10, H-6720 Szeged, Hungary;2. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;3. Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary;1. Institute of Solid State Physics, University of Latvia, 8 Kengaraga Street, Riga LV-1063, Latvia;2. Institute of Applied Chemistry, Riga Technical University, 14/24 Azenes Street, Riga LV-1048, Latvia |
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| Abstract: | An enantioselective Strecker-type reaction of imines with Et2AlCN in the presence of chiral additives has been examined. The enantioselectivity varied depending on the substituents of the imino group as well as the chiral additives used. Thus, α-aminonitriles were obtained in good yields with good enantioselectivities in the reaction of N-benzylidenebenzhydrylamine with Et2AlCN and BINOL. The reaction with excess BINOL gave the aminonitrile with reversed configuration. |
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