Premium
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.