Unconventional isomerization of allylic alcohols to allylcarbinols mediated by lanthanide catalysts

Sungyong Seo, Xianghua Yu, Tobin J. Marks*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

We report here the catalytic isomerization of aryl-substituted allylic alcohols mediated by lanthanide alkoxide complexes. The conversion yields allylcarbinols as the products of the olefin isomerization process, but with different olefinic positions than those afforded by typical transition metal catalysts. The average isolated product yields in these reactions are 65-81%. The catalytic cycle and the source of the unusual olefinic positioning are proposed to involve a strong interaction between the Lewis acidic La 3+ ion and the substrate hydroxyl group.

Original languageEnglish (US)
Pages (from-to)1828-1831
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number14
DOIs
StatePublished - Apr 3 2013

Keywords

  • Allylcarbinol
  • Allylic alcohol
  • Isomerization
  • Organolanthanide catalyst

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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