Highly diastereoselective epoxidation of allyl-substituted cycloalkenes catalyzed by metalloporphyrins

Wing Kei Chan; Peng Liu; Wing Yiu Yu; Man Kin Wong; Chi Ming Che

doi:10.1021/ol0496475

Highly diastereoselective epoxidation of allyl-substituted cycloalkenes catalyzed by metalloporphyrins

Wing Kei Chan, Peng Liu, Wing Yiu Yu, Man Kin Wong, Chi Ming Che

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

26 Citations (Scopus)

Abstract

Highly diastereoselective epoxidations of allyl-substituted cycloalkenes including allylic alcohols, esters, and amines using sterically bulky metalloporphyrins [Mn(TDCPP)Cl] (1) and [Ru(TDCPP)CO] (2) as catalysts have been achieved. The "1 + H2O2" and "2 + 2,6-Cl2pyNO" protocols afforded trans-epoxides selectively in good yields (up to 99%) with up to >99:1 trans-selectivity.

Original language	English
Pages (from-to)	1597-1599
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	10
DOIs	https://doi.org/10.1021/ol0496475
Publication status	Published - 13 May 2004
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0496475

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abstract = "Highly diastereoselective epoxidations of allyl-substituted cycloalkenes including allylic alcohols, esters, and amines using sterically bulky metalloporphyrins [Mn(TDCPP)Cl] (1) and [Ru(TDCPP)CO] (2) as catalysts have been achieved. The {"}1 + H2O2{"} and {"}2 + 2,6-Cl2pyNO{"} protocols afforded trans-epoxides selectively in good yields (up to 99%) with up to >99:1 trans-selectivity.",

author = "Chan, {Wing Kei} and Peng Liu and Yu, {Wing Yiu} and Wong, {Man Kin} and Che, {Chi Ming}",

year = "2004",

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AU - Chan, Wing Kei

AU - Liu, Peng

AU - Yu, Wing Yiu

AU - Wong, Man Kin

AU - Che, Chi Ming

PY - 2004/5/13

Y1 - 2004/5/13

N2 - Highly diastereoselective epoxidations of allyl-substituted cycloalkenes including allylic alcohols, esters, and amines using sterically bulky metalloporphyrins [Mn(TDCPP)Cl] (1) and [Ru(TDCPP)CO] (2) as catalysts have been achieved. The "1 + H2O2" and "2 + 2,6-Cl2pyNO" protocols afforded trans-epoxides selectively in good yields (up to 99%) with up to >99:1 trans-selectivity.

AB - Highly diastereoselective epoxidations of allyl-substituted cycloalkenes including allylic alcohols, esters, and amines using sterically bulky metalloporphyrins [Mn(TDCPP)Cl] (1) and [Ru(TDCPP)CO] (2) as catalysts have been achieved. The "1 + H2O2" and "2 + 2,6-Cl2pyNO" protocols afforded trans-epoxides selectively in good yields (up to 99%) with up to >99:1 trans-selectivity.

UR - http://www.scopus.com/inward/record.url?scp=2542556021&partnerID=8YFLogxK

U2 - 10.1021/ol0496475

DO - 10.1021/ol0496475

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JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Highly diastereoselective epoxidation of allyl-substituted cycloalkenes catalyzed by metalloporphyrins

Abstract

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