Preparation and nucleophilic substitution of the N,N-1,2-naphthalenedisulfonylimide derivative of a chiral amine |
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| Institution: | 1. Polish Academy of Sciences, Lodz, Poland;4. Jan Długosz University, Częstochowa, Poland;1. Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK;1. College of Laboratory Medicine, Hebei North University, 11 Diamond Street South, Zhangjiakou 075000, Hebei Province, China;2. College of Economics and Management, Hebei North University, 11 Diamond Street South, Zhangjiakou 075000, Hebei Province, China;1. College of Science, China University of Petroleum (East China), 266580 Qingdao, Shandong Province, China;2. Department of Chemical and Petroleum Engineering, University of Calgary, T2N 1N4 Calgary, Alberta, Canada;3. College of Chemical Engineering, China University of Petroleum (East China), 266580 Qingdao, Shandong Province, China |
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| Abstract: | In our series of nucleophilic substitution reactions on N,N-disulfonylimides we hereby report the preparation and the nucleophilic substitution of the N,N-1,2-naphthalenedisulfonylimide derivative 1a of the chiral amine 1. The disulfonimide was prepared by using the disulfonyl chloride reagent. Nucleophilic substitution of 1a by KNO2 and azide afforded the corresponding alcohol 2 and the azide product 3 with, respectively, 63 and 70% inversion of configuration. The stereochemical results are compared with previously reported results for a series of N,N-disulfonylimides showing that the degree of inversion of 1a is lower than for the other N,N-disulfonylimides. |
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