Asymmetric epoxidation of olefins catalyzed by chiral iminium salts generated in situ from amines and aldehydes

Man Kin Wong; Lai Mei Ho; Yan Song Zheng; Chun Yu Ho; Dan Yang

doi:10.1021/ol016260i

Asymmetric epoxidation of olefins catalyzed by chiral iminium salts generated in situ from amines and aldehydes

Man Kin Wong, Lai Mei Ho, Yan Song Zheng, Chun Yu Ho, Dan Yang

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

79 Citations (Scopus)

Abstract

(Equation presented) A new approach for catalytic asymmetric epoxidation of olefins was developed that utilized chiral iminium salts, generated in situ from chiral amines and aldehydes, as catalysts. Epoxidation reactions can be conducted with 20 mol % of amines and aldehydes. The enantioselectivity of epoxides can be up to 65%. This modular approach obviates the difficulties inherent in the preparation and isolation of unstable exocyclic iminium salts.

Original language	English
Pages (from-to)	2587-2590
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	16
DOIs	https://doi.org/10.1021/ol016260i
Publication status	Published - 9 Aug 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol016260i

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abstract = "(Equation presented) A new approach for catalytic asymmetric epoxidation of olefins was developed that utilized chiral iminium salts, generated in situ from chiral amines and aldehydes, as catalysts. Epoxidation reactions can be conducted with 20 mol % of amines and aldehydes. The enantioselectivity of epoxides can be up to 65%. This modular approach obviates the difficulties inherent in the preparation and isolation of unstable exocyclic iminium salts.",

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year = "2001",

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AU - Wong, Man Kin

AU - Ho, Lai Mei

AU - Zheng, Yan Song

AU - Ho, Chun Yu

AU - Yang, Dan

PY - 2001/8/9

Y1 - 2001/8/9

N2 - (Equation presented) A new approach for catalytic asymmetric epoxidation of olefins was developed that utilized chiral iminium salts, generated in situ from chiral amines and aldehydes, as catalysts. Epoxidation reactions can be conducted with 20 mol % of amines and aldehydes. The enantioselectivity of epoxides can be up to 65%. This modular approach obviates the difficulties inherent in the preparation and isolation of unstable exocyclic iminium salts.

AB - (Equation presented) A new approach for catalytic asymmetric epoxidation of olefins was developed that utilized chiral iminium salts, generated in situ from chiral amines and aldehydes, as catalysts. Epoxidation reactions can be conducted with 20 mol % of amines and aldehydes. The enantioselectivity of epoxides can be up to 65%. This modular approach obviates the difficulties inherent in the preparation and isolation of unstable exocyclic iminium salts.

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U2 - 10.1021/ol016260i

DO - 10.1021/ol016260i

M3 - Journal article

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JO - Organic Letters

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Asymmetric epoxidation of olefins catalyzed by chiral iminium salts generated in situ from amines and aldehydes

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