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Paper | Regular issue | Vol 63, No. 4, 2004, pp.827-844
Published online, 30th January, 2004
DOI: 10.3987/COM-03-9993
Investigation of Intramolecular Pauson-Khand Reaction of 2-Aryl-1,6- and 1-Methyl-1,7-enynes (exo-Olefins) and 1-Phenyl-1-octen-7-yne (endo-Olefin)

Miyuki Ishizaki,* Hiroshi Satoh, Osamu Hoshino, Kiyoshi Nishitani, and Hiroshi Hara*

*Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan


The intramolecular Pauson-Khand reaction of various 2-aryl-1-hepten-6-ynes and its aza-derivatives (exo-olefins) efficiently produced aryl-bicyclo[3.3.0]octenones and azaoctenone bearing quaternary carbon centers at angular positions in good yields. Although a similar reaction of 2-phenyl-1-octen-7-yne (exo-olefin), which is a homologue of 2-phenyl-1-hepten-6-yne, did not take place, the reaction of the methyl derivatives smoothly proceeded. However, the reaction of regioisomeric 1-phenyl-1-octen-7-yne (endo-olefin) afforded the desired product in moderate yields.