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N , N -1,2-Benzenedisulfonylimide, a new cyclic leaving group for the stereoselective nucleophilic substitution of amines by Karsten Sørbye; Christoffer Tautermann; Per Carlsen; Anne Fiksdahl is a Chemistry article available to read on EtoBox.

What is N , N -1,2-Benzenedisulfonylimide, a new cyclic leaving group for the stereoselective nucleophilic substitution of amines about?

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 KNO 2 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 13 C NMR using heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin as a chiral solvating agent (CSA) is discussed.

Who reads N , N -1,2-Benzenedisulfonylimide, a new cyclic leaving group for the stereoselective nucleophilic substitution of amines?

Author

Karsten Sørbye; Christoffer Tautermann; Per Carlsen; Anne Fiksdahl

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

1998

Language

EN

Field

Chemistry (Physical Sciences)