209863-91-2Relevant academic research and scientific papers
N,N-1,2-benzenedisulfonylimide, a new cyclic leaving group for the stereoselective nucleophilic substitution of amines
Sorbye, Karsten,Tautermann, Christoffer,Carlsen, Per,Fiksdahl, Anne
, p. 681 - 689 (2007/10/03)
We hereby report the preparation and nucleophilic substitutions of the N,N-1,2-benzenedisulfonylimide derivatives la 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 mines 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.
