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Scientific article
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Catalytic Intramolecular Palladium-Ene Reactions. Preliminay Communication

Published inHelvetica chimica acta, vol. 70, no. 6, p. 1477-1481
Publication date1987-09-23
First online date2004-10-25
Abstract

Pd(dba)2[dba = dibenzylideneacetone]/PPh3-or Pd(PPh3)4-catalyzed cyclizations of acetoxy-dienes 2 → 3 and 10 → 11 gave 1-vinyl-2-methylidene-subsituted cyclopentances and cyclohexanes in high yield, consistent with a palladium-ene/β-elimination mechanism (D → E → F, Scheme 2). The efficient and highly stereoselective cyclizations 7 → 7 and 8 → 9 illustrate intramolecular allylpalladium insertions into 1,2-dialkyl-, trialkyl-, trialkyl-, and cyclic alkenes followed by elimination of the exocyclic β–H giving 1,2-divinylcyclopentanes. These new olefin insertions proceed faster in AcOH (compared to THF) and occur preferentially cis relative to the Pd (13 → 14 → 15).

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Citation (ISO format)
VON OPPOLZER, Wolfgang, GAUDIN, Jean-Marc. Catalytic Intramolecular Palladium-Ene Reactions. Preliminay Communication. In: Helvetica chimica acta, 1987, vol. 70, n° 6, p. 1477–1481. doi: 10.1002/hlca.19870700604
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ISSN of the journal0018-019X
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