Chemoselective addition of isocyanides to N-tert-butanesulfinimines.

Authors :: Janssen GV
Janssen E
Vande Velde CM
Ehlers AW
Slootweg JC
Ruijter E
Lammertsma K
Orru RV
Source :: Organic letters [Org Lett] 2014 Oct 03; Vol. 16 (19), pp. 5116-9. Date of Electronic Publication: 2014 Sep 17.
Publication Year :: 2014
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.