Unconventional isomerization of allylic alcohols to allylcarbinols mediated by lanthanide catalysts

Sungyong Seo; Xianghua Yu; Tobin J. Marks

doi:10.1016/j.tetlet.2013.01.111

Unconventional isomerization of allylic alcohols to allylcarbinols mediated by lanthanide catalysts

Sungyong Seo, Xianghua Yu, Tobin J. Marks^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	1828-1831
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	14
DOIs	https://doi.org/10.1016/j.tetlet.2013.01.111
State	Published - Apr 3 2013

Keywords

Allylcarbinol
Allylic alcohol
Isomerization
Organolanthanide catalyst

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.01.111

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title = "Unconventional isomerization of allylic alcohols to allylcarbinols mediated by lanthanide catalysts",

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.",

keywords = "Allylcarbinol, Allylic alcohol, Isomerization, Organolanthanide catalyst",

author = "Sungyong Seo and Xianghua Yu and Marks, {Tobin J.}",

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TY - JOUR

T1 - Unconventional isomerization of allylic alcohols to allylcarbinols mediated by lanthanide catalysts

AU - Seo, Sungyong

AU - Yu, Xianghua

AU - Marks, Tobin J.

PY - 2013/4/3

Y1 - 2013/4/3

N2 - 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.

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.

KW - Allylcarbinol

KW - Allylic alcohol

KW - Isomerization

KW - Organolanthanide catalyst

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DO - 10.1016/j.tetlet.2013.01.111

M3 - Article

AN - SCOPUS:84875226437

SN - 0040-4039

VL - 54

SP - 1828

EP - 1831

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Unconventional isomerization of allylic alcohols to allylcarbinols mediated by lanthanide catalysts

Abstract

Keywords

ASJC Scopus subject areas

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