N,N-1,2-Benzenedisulfonylimide,a new cyclic leaving group for the stereoselective nucleophilic substitution of amines |
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| Institution: | 1. Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK;1. Chemical Engineering Department, Polytechnique Montreal, Montreal (Qc), H3T 1 J4, Canada;2. Transfers, Interfaces and Processes (TIPs), Université libre de Bruxelles, 1050 Brussels, Belgium;1. Polish Academy of Sciences, Lodz, Poland;4. Jan Długosz University, Częstochowa, Poland;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: | We hereby report the preparation and nucleophilic substitutions of the N,N-1,2-benzenedisulfonylimide derivatives 1a and 2a of the chiral amines 1 and 2. The nucleophilic attack of KNO2 afforded the respective alcohols 3 and 4 with 84–90% inversion of configuration. Nucleophilic attack by the azide ion afforded the azide products 5 and 6 which were reduced to the corresponding inverted amines 1 and 2 (94–98.5% inversion). The improved leaving group ability of the N,N-1,2-benzenedisulfonylimides compared with previously reported N,N-disulfonylimides is discussed. Chiral GLC analysis of all products is summarized and the alternative chiral analysis of product 3 by 13C NMR using heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin as a chiral solvating agent (CSA) is discussed. |
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