Asymmetric epoxidation catalyzed by D-glucose-derived uloses

Tony K.M. Shing; Gulice Y.C. Leung

doi:10.1016/S0040-4020(02)00577-X

Asymmetric epoxidation catalyzed by D-glucose-derived uloses

Tony K.M. Shing, Gulice Y.C. Leung

Department of Chemistry

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

46 Citations (Scopus)

Abstract

Three ulose catalysts (1-3) were prepared from D-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose 2 and 3 in asymmetric epoxidation was poor (up to 26% ee). Ulose 1 afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (-)-trans-stilbene oxide.

Original language	English
Pages (from-to)	7545-7552
Number of pages	8
Journal	Tetrahedron
Volume	58
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4020(02)00577-X
Publication status	Published - 2002 Sept 9

Keywords

Asymmetric epoxidation
D-glucose
Ulose

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(02)00577-X

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title = "Asymmetric epoxidation catalyzed by D-glucose-derived uloses",

abstract = "Three ulose catalysts (1-3) were prepared from D-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose 2 and 3 in asymmetric epoxidation was poor (up to 26% ee). Ulose 1 afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (-)-trans-stilbene oxide.",

keywords = "Asymmetric epoxidation, D-glucose, Ulose",

author = "Shing, {Tony K.M.} and Leung, {Gulice Y.C.}",

note = "Funding Information: This research was supported by the CUHK Direct Grant.",

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AU - Shing, Tony K.M.

AU - Leung, Gulice Y.C.

N1 - Funding Information: This research was supported by the CUHK Direct Grant.

PY - 2002/9/9

Y1 - 2002/9/9

N2 - Three ulose catalysts (1-3) were prepared from D-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose 2 and 3 in asymmetric epoxidation was poor (up to 26% ee). Ulose 1 afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (-)-trans-stilbene oxide.

AB - Three ulose catalysts (1-3) were prepared from D-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose 2 and 3 in asymmetric epoxidation was poor (up to 26% ee). Ulose 1 afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (-)-trans-stilbene oxide.

KW - Asymmetric epoxidation

KW - D-glucose

KW - Ulose

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JF - Tetrahedron

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ER -

Asymmetric epoxidation catalyzed by D-glucose-derived uloses

Abstract

Keywords

ASJC Scopus subject areas

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