PALLADIUM-CATALYZED METALLO-ENE-TYPE CYCLIZATION VINYLSTANNANE COUPLING OF 1-ACETOXY-OCTA-2,7-DIENES AND 1-ACETOXY-OCT-2-EN-7-YNES

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 en...

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Published inHelvetica chimica acta Vol. 76; no. 3; pp. 1266 - 1274
Main Authors OPPOLZER, W, RUIZMONTES, J
Format Journal Article
LanguageEnglish
Published BASEL NEW SWISS CHEMICAL SOC 12.05.1993
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
HALIDES
CHEMISTRY
ORGANOTIN REAGENTS
POLYFUSED RING-SYSTEMS
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Summary: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, monocyclic trienes 19, 20, and 21, respectively.
ISSN:0018-019X
DOI:10.1002/hlca.19930760313