N-heterocyclic carbene-catalyzed radical reactions for highly enantioselective β-hydroxylation of enals

Yuexia Zhang; Yu Du; Zhijian Huang; Jianfeng Xu; Xingxing Wu; Yuhuang Wang; Ming Wang; Song Yang; Richard D. Webster; Yonggui Robin Chi

doi:10.1021/ja511371a

N-heterocyclic carbene-catalyzed radical reactions for highly enantioselective β-hydroxylation of enals

Yuexia Zhang, Yu Du, Zhijian Huang, Jianfeng Xu, Xingxing Wu, Yuhuang Wang, Ming Wang, Song Yang, Richard D. Webster^*, Yonggui Robin Chi

^*Corresponding author for this work

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

151 Citations (Scopus)

Abstract

An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.

Original language	English
Pages (from-to)	2416-2419
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	7
DOIs	https://doi.org/10.1021/ja511371a
Publication status	Published - Feb 25 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.",

author = "Yuexia Zhang and Yu Du and Zhijian Huang and Jianfeng Xu and Xingxing Wu and Yuhuang Wang and Ming Wang and Song Yang and Webster, {Richard D.} and Chi, {Yonggui Robin}",

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AU - Zhang, Yuexia

AU - Du, Yu

AU - Huang, Zhijian

AU - Xu, Jianfeng

AU - Wu, Xingxing

AU - Wang, Yuhuang

AU - Wang, Ming

AU - Yang, Song

AU - Webster, Richard D.

AU - Chi, Yonggui Robin

PY - 2015/2/25

Y1 - 2015/2/25

N2 - An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.

AB - An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.

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JF - Journal of the American Chemical Society

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ER -

N-heterocyclic carbene-catalyzed radical reactions for highly enantioselective β-hydroxylation of enals

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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