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

Von Oppolzer, Wolfgang; Keller, Thomas; Bedoya Zurita, Manuel; Stone, Charles

doi:10.1016/S0040-4039(01)93496-3

Scientific article

Letter

English

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

ContributorsVon Oppolzer, Wolfgang; Keller, Thomas; Bedoya Zurita, Manuel; Stone, Charles

Published inTetrahedron Letters, vol. 30, no. 43, p. 5883-5886

Publication date1989

Abstract

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)).

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang et al. Diastereocontrolled nickel(0)- and palladium(0) catalyzed “metallo-ene-type” cyclizations/carbonylations. In: Tetrahedron Letters, 1989, vol. 30, n° 43, p. 5883–5886. doi: 10.1016/S0040-4039(01)93496-3

Article (Published version)

Identifiers

PID : unige:152729
DOI : 10.1016/S0040-4039(01)93496-3

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403901934963

Journal ISSN0040-4039

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

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