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Chemoselective Addition of Isocyanides to N-tert-Butanesulfinimines

Author:
Janssen, Guido V., Janssen, Elwin, Vande Velde, Christophe M. L., Ehlers, Andreas W., Slootweg, J. Chris, Ruijter, Eelco, Lammertsma, Koop, Orru, Romano V. A.
Source:
Organic letters 2014 v.16 no.19 pp. 5116-5119
ISSN:
1523-7052
Subject:
acetamides, chemical reactions, chemical structure, chemoselectivity
Abstract:
The reaction of isocyanides with N-tert-butanesulfinimines shows remarkable chemoselectivity. β-Sulfinylamino isocyanides are formed exclusively with aromatic sulfinimines, while α-sulfeneimino acetamides result when using aliphatic derivatives. A mechanism is suggested for the latter transformation, together with an explanation for the observed selectivity. Finally, a scope study is presented for this remarkably chemoselective reaction.
Agid:
5787702