147. Diastereocontrolled nickel(0)- and palladium(0) catalyzed “metallo-ene-type” cyclizations/carbonylations
     Oppolzer, W.; Keller, T. H.; Bedoya-Zurita, M.; Stone, C.
     Tetrahedron Letters 1989, 30, 5883-5886

Treatment of 1-iodo{acetoxy}-2,7-octadienes 1 and 1-iodo{acetoxy}-2-en-7-ynes 12 with Ni(COD)₂/dppb (THF/MeOH) or Pd(dba)₂/PPh₃ (AcOH, then CH₂N₂) under carbon monoxide furnished chemo- and stereoselectively either bicyclic ketoesters 7 (from 1) and 15 (from 12) or trans-substituted monocyclic products 5 (from 1) and 14 (from 12), but all-cis-hexahydroindole 11 (from acetoxycyclohexene 9).

DOI : 10.1016/S0040-4039(01)93496-3 

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