Unconventional isomerization of allylic alcohols to allylcarbinols mediated by lanthanide catalysts

Sungyong Seo, Xianghua Yu, Tobin J Marks

Research output: Contribution to journalArticle

2 Citations (Scopus)

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
Pages (from-to)1828-1831
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number14
DOIs
Publication statusPublished - Apr 3 2013

Fingerprint

Lanthanoid Series Elements
Alkenes
Isomerization
Metals
Catalysts
Hydroxyl Radical
Transition metals
Ions
Substrates
allyl alcohol
hydroxide ion

Keywords

  • Allylcarbinol
  • Allylic alcohol
  • Isomerization
  • Organolanthanide catalyst

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Unconventional isomerization of allylic alcohols to allylcarbinols mediated by lanthanide catalysts. / Seo, Sungyong; Yu, Xianghua; Marks, Tobin J.

In: Tetrahedron Letters, Vol. 54, No. 14, 03.04.2013, p. 1828-1831.

Research output: Contribution to journalArticle

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AB - 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.

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