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Issue 23, 2014
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Chiral derivatives of 1,2-benzenedisulfonimide as efficient Brønsted acid catalysts in the Strecker reaction

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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 synthesized in good overall yields (respectively 34% and 41%) by means of an eleven-step 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 have been resolved and (−)atropisomers have been demonstrated to be efficient chiral catalysts in the Strecker reaction.

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

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Publication details

The article was received on 12 Mar 2014, accepted on 07 Apr 2014 and first published on 07 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00552J
Citation: Org. Biomol. Chem., 2014,12, 3902-3911
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    Chiral derivatives of 1,2-benzenedisulfonimide as efficient Brønsted acid catalysts in the Strecker reaction

    M. Barbero, S. Cadamuro, S. Dughera and R. Torregrossa, Org. Biomol. Chem., 2014, 12, 3902
    DOI: 10.1039/C4OB00552J

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