title: Chemoselective addition of isocyanides to N-tert-butanesulfinimines.
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.
authors.affiliation: Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems (AIMMS), VU University Amsterdam , De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands.
authors.forename: Guido V
authors.initials: GV
authors.lastname: Janssen
authors.forename: Elwin
authors.initials: E
authors.lastname: Janssen
authors.forename: Christophe M L
authors.initials: CM
authors.lastname: Vande Velde
authors.forename: Andreas W
authors.initials: AW
authors.lastname: Ehlers
authors.forename: J Chris
authors.initials: JC
authors.lastname: Slootweg
authors.forename: Eelco
authors.initials: E
authors.lastname: Ruijter
authors.forename: Koop
authors.initials: K
authors.lastname: Lammertsma
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000081:Acetamides; D003486:Cyanides; D007097:Imines; D013452:Sulfonium Compounds; C522016:sulfinimine