Diastereocontrolled nickel(0)- and palladium(0) catalyzed 'metallo-ene-type' cyclizations/carbonylations

Autor: M. Bedoya-Zurita, Charles Stone, Thomas H. Keller, Wolfgang Oppolzer
Rok vydání: 1989
Předmět:
Zdroj: Tetrahedron Letters, Vol. 30, No 43 (1989) pp. 5883-5886
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93496-3
Popis: 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). Cyclizations are selectively catalyzed: 1→5 and 9→11 (Pd(0)); 1→7 and 12→15 (Ni(0)).
Databáze: OpenAIRE