The brucine N-oxide-promoted asymmetric Pauson–Khand reaction

William J Kerr; David M Lindsay; Elaine M Rankin; James S Scott; Stephen P Watson

doi:10.1016/s0040-4039(00)00357-9

The brucine N-oxide-promoted asymmetric Pauson–Khand reaction

William J Kerr, David M Lindsay, Elaine M Rankin, James S Scott, Stephen P Watson

Pure And Applied Chemistry

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

48 Citations (Scopus)

Abstract

The brucine N-oxide-mediated asymmetric Pauson–Khand reaction has been further investigated. It was found that the best levels of enantioselection were obtained with substituted propargylic alcohol complexes. The studies also revealed that when acetone or 1,2-dimethoxyethane is used as the reaction solvent, enhanced levels of enantioselectivity, up to an enantiomeric ratio of 11:89, are achieved.

Original language	English
Pages (from-to)	3229-3233
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	17
DOIs	https://doi.org/10.1016/s0040-4039(00)00357-9
Publication status	Published - 22 Apr 2000

Keywords

amine N-oxides
asymmetric synthesis
cobalt and compounds
cyclopentenones
Pauson–Khand reactions

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10.1016/s0040-4039(00)00357-9

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title = "The brucine N-oxide-promoted asymmetric Pauson–Khand reaction",

abstract = "The brucine N-oxide-mediated asymmetric Pauson–Khand reaction has been further investigated. It was found that the best levels of enantioselection were obtained with substituted propargylic alcohol complexes. The studies also revealed that when acetone or 1,2-dimethoxyethane is used as the reaction solvent, enhanced levels of enantioselectivity, up to an enantiomeric ratio of 11:89, are achieved.",

keywords = "amine N-oxides, asymmetric synthesis, cobalt and compounds, cyclopentenones, Pauson–Khand reactions",

author = "Kerr, {William J} and Lindsay, {David M} and Rankin, {Elaine M} and Scott, {James S} and Watson, {Stephen P}",

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T1 - The brucine N-oxide-promoted asymmetric Pauson–Khand reaction

AU - Kerr, William J

AU - Lindsay, David M

AU - Rankin, Elaine M

AU - Scott, James S

AU - Watson, Stephen P

PY - 2000/4/22

Y1 - 2000/4/22

N2 - The brucine N-oxide-mediated asymmetric Pauson–Khand reaction has been further investigated. It was found that the best levels of enantioselection were obtained with substituted propargylic alcohol complexes. The studies also revealed that when acetone or 1,2-dimethoxyethane is used as the reaction solvent, enhanced levels of enantioselectivity, up to an enantiomeric ratio of 11:89, are achieved.

AB - The brucine N-oxide-mediated asymmetric Pauson–Khand reaction has been further investigated. It was found that the best levels of enantioselection were obtained with substituted propargylic alcohol complexes. The studies also revealed that when acetone or 1,2-dimethoxyethane is used as the reaction solvent, enhanced levels of enantioselectivity, up to an enantiomeric ratio of 11:89, are achieved.

KW - amine N-oxides

KW - asymmetric synthesis

KW - cobalt and compounds

KW - cyclopentenones

KW - Pauson–Khand reactions

U2 - 10.1016/s0040-4039(00)00357-9

DO - 10.1016/s0040-4039(00)00357-9

M3 - Article

VL - 41

SP - 3229

EP - 3233

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 17

ER -

The brucine N-oxide-promoted asymmetric Pauson–Khand reaction

Abstract

Keywords

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