Two chiral derivatives of 1,2-benzenedisulfonimide, namely 4-methyl-3,6-bis(o-tolyl)-1,2-benzenedisulfonimide and 4,5-dimethyl-3,6-bis(o-tolyl)-1,2-benzenedisulfonimide have been easily synthetized in good overall yields (respectively 34% and 41%) by means of an eleven steps synthetic protocol from commercially available 2-methyl-6-nitroaniline or 2,3-dimethyl-6-nitroaniline. 4,5-Dimethyl-3,6-bis(1-naphthyl)-1,2-benzenedisulfonimide was also synthesized but the overall yield from 2,3-dimethyl-6-nitroaniline was lower (9%). The atropisomers of these compounds has been resolved and (-) atropisomers have been demonstrated to be efficient chiral catalysts in Strecker reaction

Chiral derivatives of 1,2-benzenedisulfonimide as efficient Brønsted acid catalysts in the Strecker reaction

BARBERO, Margherita;CADAMURO, Silvano;DUGHERA, Stefano;
2014-01-01

Abstract

Two chiral derivatives of 1,2-benzenedisulfonimide, namely 4-methyl-3,6-bis(o-tolyl)-1,2-benzenedisulfonimide and 4,5-dimethyl-3,6-bis(o-tolyl)-1,2-benzenedisulfonimide have been easily synthetized in good overall yields (respectively 34% and 41%) by means of an eleven steps synthetic protocol from commercially available 2-methyl-6-nitroaniline or 2,3-dimethyl-6-nitroaniline. 4,5-Dimethyl-3,6-bis(1-naphthyl)-1,2-benzenedisulfonimide was also synthesized but the overall yield from 2,3-dimethyl-6-nitroaniline was lower (9%). The atropisomers of these compounds has been resolved and (-) atropisomers have been demonstrated to be efficient chiral catalysts in Strecker reaction
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http://pubs.rsc.org/en/journals/journalissues/ob#!recentarticles&all
Sulfonimides; Brønsted acids; Asymmetric catalysis; Strecker reaction; Atropisomerism
Margherita Barbero; Silvano Cadamuro; Stefano Dughera; Roberta Torregrossa
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/147964
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