title: Azepine synthesis from alkyl azide and propargylic ester via gold catalysis.
abstract: An efficient new method was developed to synthesize multisubstituted 4,5-dihydro-1H-azepine derivatives through the gold-catalyzed reaction of two molecules of propargylic esters with one molecule of alkyl azide. It was proposed that vinyl gold carbenoid, in situ generated from propargylic ester through gold-catalyzed 1,2-rearrangement, was trapped by alkyl azide to give vinyl imine intermediate. These, in turn, could undergo a formal [4 + 3] cycloaddition with another molecule of vinyl gold carbenoid to afford the desired azepine product.
authors.affiliation: Department of Chemistry, Renmin University of China, Beijing 100872, PR China.
authors.forename: Heng
authors.initials: H
authors.lastname: Liu
authors.forename: Xin
authors.initials: X
authors.lastname: Li
authors.forename: Zili
authors.initials: Z
authors.lastname: Chen
authors.forename: Wen-Xiang
authors.initials: WX
authors.lastname: Hu
mesh_terms: D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004952:Esters; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001381:Azepines; D001386:Azides; D004952:Esters; D006046:Gold