Homoallyllic nitrone isomerization: Convenient enantioselective synthesis of homoallylic nitrones and homoallylic hydroxylamines

Hin Soon Cheng; Ai Hua Seow; Teck Peng Loh

doi:10.1021/ol800925v

Homoallyllic nitrone isomerization: Convenient enantioselective synthesis of homoallylic nitrones and homoallylic hydroxylamines

Hin Soon Cheng, Ai Hua Seow, Teck Peng Loh^*

^*Corresponding author for this work

Nanyang Technological University

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

17 Citations (Scopus)

Abstract

(Chemical Equation Presented) An α-regioselective synthesis of homoallylic nitrones from aldehydes is reported on the basis of [3,3]-sigmatropic rearrangement. The products are obtained in up to 99% enantioselectivity and up to 80% yield under environmentally benign and mild reaction conditions.

Original language	English
Pages (from-to)	2805-2807
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	13
DOIs	https://doi.org/10.1021/ol800925v
Publication status	Published - 2008
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol800925v

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title = "Homoallyllic nitrone isomerization: Convenient enantioselective synthesis of homoallylic nitrones and homoallylic hydroxylamines",

abstract = "(Chemical Equation Presented) An α-regioselective synthesis of homoallylic nitrones from aldehydes is reported on the basis of [3,3]-sigmatropic rearrangement. The products are obtained in up to 99% enantioselectivity and up to 80% yield under environmentally benign and mild reaction conditions.",

author = "Cheng, {Hin Soon} and Seow, {Ai Hua} and Loh, {Teck Peng}",

year = "2008",

doi = "10.1021/ol800925v",

language = "English",

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journal = "Organic Letters",

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T1 - Homoallyllic nitrone isomerization

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AU - Cheng, Hin Soon

AU - Seow, Ai Hua

AU - Loh, Teck Peng

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) An α-regioselective synthesis of homoallylic nitrones from aldehydes is reported on the basis of [3,3]-sigmatropic rearrangement. The products are obtained in up to 99% enantioselectivity and up to 80% yield under environmentally benign and mild reaction conditions.

AB - (Chemical Equation Presented) An α-regioselective synthesis of homoallylic nitrones from aldehydes is reported on the basis of [3,3]-sigmatropic rearrangement. The products are obtained in up to 99% enantioselectivity and up to 80% yield under environmentally benign and mild reaction conditions.

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DO - 10.1021/ol800925v

M3 - Article

AN - SCOPUS:59949083245

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Homoallyllic nitrone isomerization: Convenient enantioselective synthesis of homoallylic nitrones and homoallylic hydroxylamines

Abstract

ASJC Scopus Subject Areas

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