title: A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.
abstract: A novel mode of reactivity for the diazo group, the 1,3-addition of a nucleophile and an electrophile to the diazo group, has been realized in the intramolecular aminoalkylation of β-amino-α-diazoesters to form tetrasubstituted 1,2,3-triazolines. The reaction exhibited a broad scope, good functional group tolerance, and excellent diastereoselectivity. In addition, a new Au-catalyzed intramolecular transannulation reaction of the obtained propargyl triazolines to give pyrroles has been discovered.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Room 4500 SES, Chicago (USA) http://www.chem.uic.edu/vggroup.
authors.forename: Alexey
authors.initials: A
authors.lastname: Kuznetsov
authors.forename: Anton V
authors.initials: AV
authors.lastname: Gulevich
authors.forename: Donald J
authors.initials: DJ
authors.lastname: Wink
authors.forename: Vladimir
authors.initials: V
authors.lastname: Gevorgyan
mesh_terms: D000478:Alkylation; D000588:Amines / Q000737:chemistry; D013058:Mass Spectrometry; D011758:Pyrroles / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D011758:Pyrroles; D015363:Quinolones; D014230:Triazoles
keywords: aminoalkylation; diastereoselectivity; diazo compounds; heterocycles; triazolines