Selective Cross-Metathesis Versus Ring-Closing Metathesis of Terpenes, Taking the Path Less Travelled

Keren Iudanov, Noy B. Nechmad, Albert Poater, N. Gabriel Lemcoff

Research output: Contribution to journalArticlepeer-review

Abstract

A diiodo ruthenium olefin metathesis pre-catalyst was employed to achieve remarkably selective cross-metathesis reactions of prenylated 1,6-dienes, effectively overcoming the entropically favored intramolecular ring-closing metathesis. This reaction was investigated using Density Functional Theory (DFT) computations and fine-tuned through the application of a Design of Experiments (DoE) approach. The potential of this innovative process was demonstrated through the unprecedented functionalization of various terpene natural products via cross-metathesis, resulting in the synthesis of new derivatives in a single step.

Original languageAmerican English
Article numbere202412430
JournalAngewandte Chemie - International Edition
Volume63
Issue number52
DOIs
StatePublished - 20 Dec 2024

Keywords

  • cross-metathesis
  • iodide ligands
  • olefin metathesis
  • sulfur-chelated ruthenium
  • terpenes

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Catalysis

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