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Highly catalyst-dependent cycloisomerisation of an O-tethered enyne derived from nerol

Paper ID Volume ID Publish Year Pages File Format Full-Text
51170 46833 2010 5 PDF Available
Title
Highly catalyst-dependent cycloisomerisation of an O-tethered enyne derived from nerol
Abstract

The cycloisomerisation of an O-tethered enyne derived from nerol has been studied using various catalytic systems such as PtCl2, AuCl3, {[AuCl(PPh3)]/AgPF6} and [Rh2Cl2(CO)4]. Whatever the catalyst used, formal Alder-ene 1,4-dienes were obtained as major products along with cyclopropane and 1,3-diene derivatives, indicating the crucial influence of the structure of the enyne substrate on the course of the reaction. Differences in terms of activity and selectivity nevertheless appeared when moving from Rh- or Pt-based catalysts to Au(I)-based catalysts: mechanistic pathways are proposed to explain these observations.

Graphical AbstractFigure optionsDownload full-size imageDownload as PowerPoint slideResearch Highlights►PtCl2, {[AuCl(PPh3)]/AgPF6} and [Rh2Cl2(CO)4] catalyse the cycloisomerisation of a nerol-derived O-tethered enyne. ►Formal Alder-ene 1,4-dienes are obtained as major products in the cycloisomerisation of a nerol-derived O-tethered enyne. ►Differences in terms of activity and selectivity appeared when moving from Rh- or Pt- to Au(I)-based catalysts.

Keywords
Monoterpenes; Enyne cycloisomerisation; Rhodium; Platinum; Gold; Homogeneous catalysis
First Page Preview
Highly catalyst-dependent cycloisomerisation of an O-tethered enyne derived from nerol
Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 12, Issue 2, 15 November 2010, Pages 142–146
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis