Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

Hongling Wang; Yuhuang Wang; Xingkuan Chen; Chengli Mou; Shuyan Yu; Huifang Chai; Zhichao Jin; Yonggui Robin Chi

doi:10.1021/acs.orglett.9b02736

Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

Hongling Wang, Yuhuang Wang, Xingkuan Chen, Chengli Mou, Shuyan Yu, Huifang Chai^*, Zhichao Jin, Yonggui Robin Chi

^*Corresponding author for this work

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

38 Citations (Scopus)

Abstract

A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions.

Original language	English
Pages (from-to)	7440-7444
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.9b02736
Publication status	Published - Sept 20 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions.",

author = "Hongling Wang and Yuhuang Wang and Xingkuan Chen and Chengli Mou and Shuyan Yu and Huifang Chai and Zhichao Jin and Chi, {Yonggui Robin}",

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T1 - Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

AU - Wang, Hongling

AU - Wang, Yuhuang

AU - Chen, Xingkuan

AU - Mou, Chengli

AU - Yu, Shuyan

AU - Chai, Huifang

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2019/9/20

Y1 - 2019/9/20

N2 - A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions.

AB - A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions.

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SN - 1523-7060

VL - 21

SP - 7440

EP - 7444

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

Abstract

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