Enantioselective Thia-Wolff Rearrangement via Cooperative Catalysis of Rhodium/Chiral Brønsted Acid: A Facile Access to Enantioenriched α-Sulfenylated Amides†

Zhi Yao Si; Xun Shen Liu; Yuting Zhao; Yuhao Ni; Yuxuan Cao; Yuanjing Xiao; Lu Liu

doi:10.1002/cjoc.70328

Enantioselective Thia-Wolff Rearrangement via Cooperative Catalysis of Rhodium/Chiral Brønsted Acid: A Facile Access to Enantioenriched α-Sulfenylated Amides^†

Zhi Yao Si, Xun Shen Liu, Yuting Zhao, Yuhao Ni, Yuxuan Cao, Yuanjing Xiao, Lu Liu

School of Chemistry and Molecular Engineering

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

1 Scopus citations

Abstract

The first catalytic asymmetric thia-Wolff rearrangement between α-aryl α-diazothioesters and amines has been successfully achieved under cooperative rhodium/chiral phosphoric acid catalysis, which provides efficient access to synthetically valuable chiral α-sulfenylated amide architectures. This protocol features mild reaction conditions, high efficiency, excellent stereoselectivity, and a broad substrate scope.

Original language	English
Journal	Chinese Journal of Chemistry
DOIs	https://doi.org/10.1002/cjoc.70328
State	Accepted/In press - 2025

Keywords

Carbene
Chiral Brønsted acid
Diazothioesters
Wolff rearrangement
α-Sulfenylated amides

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10.1002/cjoc.70328

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title = "Enantioselective Thia-Wolff Rearrangement via Cooperative Catalysis of Rhodium/Chiral Br{\o}nsted Acid: A Facile Access to Enantioenriched α-Sulfenylated Amides†",

abstract = "The first catalytic asymmetric thia-Wolff rearrangement between α-aryl α-diazothioesters and amines has been successfully achieved under cooperative rhodium/chiral phosphoric acid catalysis, which provides efficient access to synthetically valuable chiral α-sulfenylated amide architectures. This protocol features mild reaction conditions, high efficiency, excellent stereoselectivity, and a broad substrate scope.",

keywords = "Carbene, Chiral Br{\o}nsted acid, Diazothioesters, Wolff rearrangement, α-Sulfenylated amides",

author = "Si, \{Zhi Yao\} and Liu, \{Xun Shen\} and Yuting Zhao and Yuhao Ni and Yuxuan Cao and Yuanjing Xiao and Lu Liu",

note = "Publisher Copyright: {\textcopyright} 2025 SIOC, CAS, Shanghai, \& WILEY-VCH GmbH.",

year = "2025",

doi = "10.1002/cjoc.70328",

language = "英语",

journal = "Chinese Journal of Chemistry",

issn = "1001-604X",

publisher = "John Wiley and Sons Inc",

}

TY - JOUR

T1 - Enantioselective Thia-Wolff Rearrangement via Cooperative Catalysis of Rhodium/Chiral Brønsted Acid

T2 - A Facile Access to Enantioenriched α-Sulfenylated Amides†

AU - Si, Zhi Yao

AU - Liu, Xun Shen

AU - Zhao, Yuting

AU - Ni, Yuhao

AU - Cao, Yuxuan

AU - Xiao, Yuanjing

AU - Liu, Lu

PY - 2025

Y1 - 2025

N2 - The first catalytic asymmetric thia-Wolff rearrangement between α-aryl α-diazothioesters and amines has been successfully achieved under cooperative rhodium/chiral phosphoric acid catalysis, which provides efficient access to synthetically valuable chiral α-sulfenylated amide architectures. This protocol features mild reaction conditions, high efficiency, excellent stereoselectivity, and a broad substrate scope.

AB - The first catalytic asymmetric thia-Wolff rearrangement between α-aryl α-diazothioesters and amines has been successfully achieved under cooperative rhodium/chiral phosphoric acid catalysis, which provides efficient access to synthetically valuable chiral α-sulfenylated amide architectures. This protocol features mild reaction conditions, high efficiency, excellent stereoselectivity, and a broad substrate scope.

KW - Carbene

KW - Chiral Brønsted acid

KW - Diazothioesters

KW - Wolff rearrangement

KW - α-Sulfenylated amides

UR - https://www.scopus.com/pages/publications/105019785964

U2 - 10.1002/cjoc.70328

DO - 10.1002/cjoc.70328

M3 - 文章

AN - SCOPUS:105019785964

SN - 1001-604X

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

ER -

Enantioselective Thia-Wolff Rearrangement via Cooperative Catalysis of Rhodium/Chiral Brønsted Acid: A Facile Access to Enantioenriched α-Sulfenylated Amides^†

Abstract

Keywords

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