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Catalytic Intramolecular Palladium‐Ene Reactions. Preliminay Communication
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AbstractPd(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).
Title: Catalytic Intramolecular Palladium‐Ene Reactions. Preliminay Communication
Description:
AbstractPd(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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