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Scientific article
English

Palladium-catalyzed intramolecular olefin allylations: stereocontrolled syntheses of bicyclic systems and evidence for an allylpalladium/olefin-cis-insertion

Published inTetrahedron letters, vol. 29, no. 37, p. 4705-4708
Publication date1988
Abstract

Pd(O)-catalyzed cyclizations of (1-acetoxy-3-alkenyl)-2-cycloalkenes 3, 6 and 12 provide bicyclic systems in high diastereo- (5, 8) and enantio-meric (14) purity consistent with a predominant allylpalladium/alkene cis- insertion. Pd (o)-catalyzed, stereospecific (3 → 5,6 → 8) and enantiospecific (12 → 14) cyclizations are consistent with allylpalladium/alkene cis-insertions of 4, 7, 13 and represent a new approach to either cis - or trans-fused ring systems.

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Citation (ISO format)
VON OPPOLZER, Wolfgang, GAUDIN, Jean-Marc, BIRKINSHAW, Timothy Nicholas. Palladium-catalyzed intramolecular olefin allylations: stereocontrolled syntheses of bicyclic systems and evidence for an allylpalladium/olefin-cis-insertion. In: Tetrahedron letters, 1988, vol. 29, n° 37, p. 4705–4708. doi: 10.1016/S0040-4039(00)80586-9
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