Palladium‐Catalyzed ‘Metallo‐Ene’‐Type Cyclization/Vinylstannane Coupling of 1‐Acetoxy‐octa‐2,7‐dienes and 1‐Acetoxy‐oct‐2‐en‐7‐ynes | Zendy

Oppolzer Wolfgang | Zendy; RuizMontes José | Zendy

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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

Author(s) -

Oppolzer Wolfgang,

RuizMontes José

Publication year - 1993

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19930760313

Subject(s) - chemistry , stannane , palladium , catalysis , medicinal chemistry , ene reaction , phosphine , intramolecular force , stereochemistry , organic chemistry

Palladiumbis(dibenzylideneacetone)/tri(2‐furyl)phosphine‐catalyzed cyclizations of dienyl acetates 2 in the presence of an (1‐alkenyl)(tributyl)stannane and ZnCl 2 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.

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