Mimicking polyolefin carbocyclization reactions: gold-catalyzed intramolecular phenoxycyclization of 1,5-enynes.
PPh(3)AuNTf(2) promotes highly efficient intramolecular phenoxycyclization reactions on 1,5-enynes under mild conditions. The original tricyclic and functionalized heterocycles were isolated in good to excellent yields. The 6-endo cyclization process is predominant and operates via a biomimetic cascade cation-olefin process. The efficiency of this system was further demonstrated in the cycloisomerization reaction of a 1,5,9-dienyne.
Toullec
Patrick Yves
PY
Laboratoire Charles Friedel, UMR 7223, Ecole Nationale Supérieure de Chimie de Paris, 11, rue P. et M. Curie, 75231 Paris Cedex 05, France.
Blarre
Thomas
T
Michelet
Véronique
V
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D015394:Molecular Structure
D000480:Alkynes; D006046:Gold