Synthesis of azepines by a gold-catalyzed intermolecular [4 + 3]-annulation.
A convenient gold(III)-catalyzed synthesis of azepines from the intermolecular annulation of propargyl esters and alpha,beta-unsaturated imines is reported (19 examples, 55-95% yield). This formal [4 + 3]-cycloaddition reaction is proposed to proceed via a stepwise process involving intramolecular trapping of an allyl-gold intermediate.
Shapiro
Nathan D
ND
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Toste
F Dean
FD
D000498:Allyl Compounds / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry
D000498:Allyl Compounds; D001381:Azepines; D009942:Organometallic Compounds; D006046:Gold