Palladium-Catalyzed "Metallo-Ene"-Type Cyclization/Vinylstannane Coupling of 1-Acetoxy-octa-2,7-dienes and 1-Acetoxy-oct-2-en-7-ynes

Von Oppolzer, Wolfgang; Ruiz-montes, José

doi:10.1002/hlca.19930760313

Scientific article

English

Palladium-Catalyzed "Metallo-Ene"-Type Cyclization/Vinylstannane Coupling of 1-Acetoxy-octa-2,7-dienes and 1-Acetoxy-oct-2-en-7-ynes

ContributorsVon Oppolzer, Wolfgang; Ruiz-montes, José

Published inHelvetica chimica acta, vol. 76, no. 3, p. 1266-1274

Publication date1993

Abstract

Palladiumbis(dibenzylideneacetone)/tri(2-furyl)phosphine-catalyzed cyclizations of dienyl acetates 2 in the presence of an (1-alkenyl)(tributyl)stannane and ZnCl2 provided trans-substituted 3-alkenyl-4-vinylcyclopentanes 11 in good yields. Analogous intramolecular carbometallation/C,C-coupling of enynyl acetates 4, 6, and 8 furnished, stereospecifically, monocylic trienes 19, 20, and 21, respectively.

Affiliation

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, RUIZ-MONTES, José. Palladium-Catalyzed ‘Metallo-Ene’-Type Cyclization/Vinylstannane Coupling of 1-Acetoxy-octa-2,7-dienes and 1-Acetoxy-oct-2-en-7-ynes. In: Helvetica chimica acta, 1993, vol. 76, n° 3, p. 1266–1274. doi: 10.1002/hlca.19930760313

Article (Published version)

Identifiers

PID : unige:86083
DOI : 10.1002/hlca.19930760313

ISSN of the journal0018-019X

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Palladium-Catalyzed "Metallo-Ene"-Type Cyclization/Vinylstannane Coupling of 1-Acetoxy-octa-2,7-dienes and 1-Acetoxy-oct-2-en-7-ynes

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