Chiral ruthenium-oxo complexes for enantioselective epoxidation of trans-stilbene

Wing Yiu Yu; Wai Hong Fung; Jia Ling Zhu; Kung Kai Cheung; Kwok Keung Ho; Chi Ming Che

doi:10.1002/jccs.199900050

Chiral ruthenium-oxo complexes for enantioselective epoxidation of trans-stilbene

Wing Yiu Yu, Wai Hong Fung, Jia Ling Zhu, Kung Kai Cheung, Kwok Keung Ho, Chi Ming Che

Research output: Journal article publication › Journal article › Academic research › peer-review

14 Citations (Scopus)

Abstract

Two oxoruthenium(IV) complexes containing C2symmetric 1,1′-biisoquinoline (biqn) and (R,R)-3,3′-(1,2-dimethylethylenedioxy)-2,2′-bipyridine (diopy*) were prepared, and both are active oxidants for alkene epoxidations. The oxidation of styrene and cis- and trans-β-methylstyrenes by [(Cn)(diopy*)-RuIV(O)](ClO4)2did not proceed enantioselectively, but the same oxidant can attain a moderate enantioselectivity of 33%ee for the trans-stilbene oxidation to trans-stilbene oxide. A head-on approach model, where the C=C is directed from the top to the O=Ru moiety, is proposed to account for the facial differentiation of the trans-stilbene oxidation.

Original language	English
Pages (from-to)	341-349
Number of pages	9
Journal	Journal of the Chinese Chemical Society
Volume	46
Issue number	3
DOIs	https://doi.org/10.1002/jccs.199900050
Publication status	Published - 1 Jan 1999
Externally published	Yes

Keywords

Asymmetric epoxidation
Oxidation
Ruthenium
Trans-stilbene

ASJC Scopus subject areas

General Chemistry

More information

10.1002/jccs.199900050

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title = "Chiral ruthenium-oxo complexes for enantioselective epoxidation of trans-stilbene",

abstract = "Two oxoruthenium(IV) complexes containing C2symmetric 1,1′-biisoquinoline (biqn) and (R,R)-3,3′-(1,2-dimethylethylenedioxy)-2,2′-bipyridine (diopy*) were prepared, and both are active oxidants for alkene epoxidations. The oxidation of styrene and cis- and trans-β-methylstyrenes by [(Cn)(diopy*)-RuIV(O)](ClO4)2did not proceed enantioselectively, but the same oxidant can attain a moderate enantioselectivity of 33%ee for the trans-stilbene oxidation to trans-stilbene oxide. A head-on approach model, where the C=C is directed from the top to the O=Ru moiety, is proposed to account for the facial differentiation of the trans-stilbene oxidation.",

keywords = "Asymmetric epoxidation, Oxidation, Ruthenium, Trans-stilbene",

author = "Yu, {Wing Yiu} and Fung, {Wai Hong} and Zhu, {Jia Ling} and Cheung, {Kung Kai} and Ho, {Kwok Keung} and Che, {Chi Ming}",

year = "1999",

month = jan,

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doi = "10.1002/jccs.199900050",

language = "English",

volume = "46",

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journal = "Journal of the Chinese Chemical Society",

issn = "0009-4536",

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T1 - Chiral ruthenium-oxo complexes for enantioselective epoxidation of trans-stilbene

AU - Yu, Wing Yiu

AU - Fung, Wai Hong

AU - Zhu, Jia Ling

AU - Cheung, Kung Kai

AU - Ho, Kwok Keung

AU - Che, Chi Ming

PY - 1999/1/1

Y1 - 1999/1/1

N2 - Two oxoruthenium(IV) complexes containing C2symmetric 1,1′-biisoquinoline (biqn) and (R,R)-3,3′-(1,2-dimethylethylenedioxy)-2,2′-bipyridine (diopy*) were prepared, and both are active oxidants for alkene epoxidations. The oxidation of styrene and cis- and trans-β-methylstyrenes by [(Cn)(diopy*)-RuIV(O)](ClO4)2did not proceed enantioselectively, but the same oxidant can attain a moderate enantioselectivity of 33%ee for the trans-stilbene oxidation to trans-stilbene oxide. A head-on approach model, where the C=C is directed from the top to the O=Ru moiety, is proposed to account for the facial differentiation of the trans-stilbene oxidation.

AB - Two oxoruthenium(IV) complexes containing C2symmetric 1,1′-biisoquinoline (biqn) and (R,R)-3,3′-(1,2-dimethylethylenedioxy)-2,2′-bipyridine (diopy*) were prepared, and both are active oxidants for alkene epoxidations. The oxidation of styrene and cis- and trans-β-methylstyrenes by [(Cn)(diopy*)-RuIV(O)](ClO4)2did not proceed enantioselectively, but the same oxidant can attain a moderate enantioselectivity of 33%ee for the trans-stilbene oxidation to trans-stilbene oxide. A head-on approach model, where the C=C is directed from the top to the O=Ru moiety, is proposed to account for the facial differentiation of the trans-stilbene oxidation.

KW - Asymmetric epoxidation

KW - Oxidation

KW - Ruthenium

KW - Trans-stilbene

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U2 - 10.1002/jccs.199900050

DO - 10.1002/jccs.199900050

M3 - Journal article

SN - 0009-4536

VL - 46

SP - 341

EP - 349

JO - Journal of the Chinese Chemical Society

JF - Journal of the Chinese Chemical Society

IS - 3

ER -

Chiral ruthenium-oxo complexes for enantioselective epoxidation of trans-stilbene

Abstract

Keywords

ASJC Scopus subject areas

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