New pinene-derived pyridines as bidentate chiral ligands

A.V. Malkov; A.J.P. Stewart-Liddon; F. Teply; L. Kobr; K.W. Muir; David Haigh; P. Kocovsky

doi:10.1016/j.tet.2008.02.045

New pinene-derived pyridines as bidentate chiral ligands

A.V. Malkov, A.J.P. Stewart-Liddon, F. Teply, L. Kobr, K.W. Muir, David Haigh, P. Kocovsky

Research output: Contribution to journal › Article › peer-review

51 Citations (Scopus)

Abstract

A synthesis of new bidentate pyridines has been developed, starting from ?-pinene. A copper complex of the pyridine-oxazoline ligands catalyzes asym. allylic oxidn. of cyclic olefins with good conversion rates and acceptable enantioselectivity (?67% ee). The imidazolium salt I has been identified as a precursor of the N,N'-unsym. N-heterocyclic carbene ligand, which upon complexation with palladium, catalyzed the intramol. amide enolate ?-arylation leading to oxindole in excellent yield but with low enantioselectivity.

Original language	English
Pages (from-to)	4011-4025
Number of pages	15
Journal	Tetrahedron
Volume	64
Issue number	18
DOIs	https://doi.org/10.1016/j.tet.2008.02.045
Publication status	Published - 28 Apr 2008

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/j.tet.2008.02.045

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abstract = "A synthesis of new bidentate pyridines has been developed, starting from ?-pinene. A copper complex of the pyridine-oxazoline ligands catalyzes asym. allylic oxidn. of cyclic olefins with good conversion rates and acceptable enantioselectivity (?67% ee). The imidazolium salt I has been identified as a precursor of the N,N'-unsym. N-heterocyclic carbene ligand, which upon complexation with palladium, catalyzed the intramol. amide enolate ?-arylation leading to oxindole in excellent yield but with low enantioselectivity.",

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T1 - New pinene-derived pyridines as bidentate chiral ligands

AU - Malkov, A.V.

AU - Stewart-Liddon, A.J.P.

AU - Teply, F.

AU - Kobr, L.

AU - Muir, K.W.

AU - Haigh, David

AU - Kocovsky, P.

PY - 2008/4/28

Y1 - 2008/4/28

N2 - A synthesis of new bidentate pyridines has been developed, starting from ?-pinene. A copper complex of the pyridine-oxazoline ligands catalyzes asym. allylic oxidn. of cyclic olefins with good conversion rates and acceptable enantioselectivity (?67% ee). The imidazolium salt I has been identified as a precursor of the N,N'-unsym. N-heterocyclic carbene ligand, which upon complexation with palladium, catalyzed the intramol. amide enolate ?-arylation leading to oxindole in excellent yield but with low enantioselectivity.

AB - A synthesis of new bidentate pyridines has been developed, starting from ?-pinene. A copper complex of the pyridine-oxazoline ligands catalyzes asym. allylic oxidn. of cyclic olefins with good conversion rates and acceptable enantioselectivity (?67% ee). The imidazolium salt I has been identified as a precursor of the N,N'-unsym. N-heterocyclic carbene ligand, which upon complexation with palladium, catalyzed the intramol. amide enolate ?-arylation leading to oxindole in excellent yield but with low enantioselectivity.

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DO - 10.1016/j.tet.2008.02.045

M3 - Article

SN - 0040-4020

VL - 64

SP - 4011

EP - 4025

JO - Tetrahedron

JF - Tetrahedron

IS - 18

ER -

New pinene-derived pyridines as bidentate chiral ligands

Abstract

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