Enantioselective aza-Henry reaction using cinchona organocatalysts |
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| Institution: | 1. Department of Organic Chemistry ‘A. Mangini’, University of Bologna, Viale Risorgimento No 4, I-40136 Bologna, Italy;2. Universidad de Alicante, Dpto. Quimica Organica, Apdo. 99, 03080-Alicante, Spain;1. National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;2. School of Pharmacy, Zunyi Medical University, Zunyi 563000, China;3. University of Chinese Academy of Sciences, Beijing 100049, China;1. Key Laboratory of Applied Surface and Colloid Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, Shaanxi 710062, PR China;2. Department of Medical Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, Shaanxi 710032, PR China;1. School of Chemistry&Molecular Engineering, East China University of Science&Technology, 130 Meilong Road, Shanghai 200237, China;2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;1. Middle East Technical University, Department of Chemistry, 06800 Ankara, Turkey;2. Selçuk University, Department of Chemistry, 42031 Konya, Turkey;1. School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China;2. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China |
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| Abstract: | The aza-Henry reaction of imines with nitromethane was promoted by cinchona alkaloids and modified cinchona bases to give optically active β-nitroamines. Various N-protected imines were examined as substrates. N-Boc, N-Cbz, and N-Fmoc protected imines gave the best results in terms of chemical yields and enantioselectivities. After a careful screening of a series of chiral bases, very good enantioselectivities up to 94% ee were obtained using a cinchona-based thiourea organocatalyst under the optimized reaction conditions. |
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