379686-28-9Relevant academic research and scientific papers
Stereoselective transformation of amines via chiral 2,4,6-triphenylpyridinium intermediates
Said, Sadri A.,Fiksdahl, Anne
, p. 1947 - 1951 (2007/10/03)
We herein report the preparation and the nucleophilic substitution of the chiral 2,4,6-triphenylpyridinium tetrafluoroborates 2a and 2b. The triphenylpyridinium intermediates were generated from homochiral amines (1a, 1b) and 2,4,6-triphenylpyrylium tetrafluoroborate and used as substrates for stereoselective nucleophilic substitution. The degree of inversion in the substitution reactions has been studied. The alcohol (3a, 3b) and azide (4a, 4b) products were obtained with >99 and 96-98% inversion of configuration, respectively.
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.
