Decarboxylative Coupling of Ketoacids with Allylic Acetates

Xiaoyu Zhang; Fanyi Hou; Yinlei Zhang; Bowen Li; Peizhong Xie; Teck Peng Loh

doi:10.1021/acs.orglett.4c03514

Decarboxylative Coupling of Ketoacids with Allylic Acetates

Xiaoyu Zhang, Fanyi Hou, Yinlei Zhang, Bowen Li, Peizhong Xie^*, Teck Peng Loh^*

^*Corresponding author for this work

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

1 Citation (Scopus)

Abstract

We developed a novel, metal-free catalytic system for synthesizing a broad range of itaconates using α-ketoacids and allylic acetate. This method, leveraging phosphine and Mes-Acr⁺(BF₄^-) catalysts, has proven versatile, enabling the efficient itaconation of peptides, the synthesis of bioactive itaconates, and the preparation of an itaconate-based bio-orthogonal probe.

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.4c03514
Publication status	Accepted/In press - 2024
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2024 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.4c03514

Cite this

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title = "Decarboxylative Coupling of Ketoacids with Allylic Acetates",

abstract = "We developed a novel, metal-free catalytic system for synthesizing a broad range of itaconates using α-ketoacids and allylic acetate. This method, leveraging phosphine and Mes-Acr+(BF4-) catalysts, has proven versatile, enabling the efficient itaconation of peptides, the synthesis of bioactive itaconates, and the preparation of an itaconate-based bio-orthogonal probe.",

author = "Xiaoyu Zhang and Fanyi Hou and Yinlei Zhang and Bowen Li and Peizhong Xie and Loh, {Teck Peng}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

doi = "10.1021/acs.orglett.4c03514",

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Decarboxylative Coupling of Ketoacids with Allylic Acetates

AU - Zhang, Xiaoyu

AU - Hou, Fanyi

AU - Zhang, Yinlei

AU - Li, Bowen

AU - Xie, Peizhong

AU - Loh, Teck Peng

PY - 2024

Y1 - 2024

N2 - We developed a novel, metal-free catalytic system for synthesizing a broad range of itaconates using α-ketoacids and allylic acetate. This method, leveraging phosphine and Mes-Acr+(BF4-) catalysts, has proven versatile, enabling the efficient itaconation of peptides, the synthesis of bioactive itaconates, and the preparation of an itaconate-based bio-orthogonal probe.

AB - We developed a novel, metal-free catalytic system for synthesizing a broad range of itaconates using α-ketoacids and allylic acetate. This method, leveraging phosphine and Mes-Acr+(BF4-) catalysts, has proven versatile, enabling the efficient itaconation of peptides, the synthesis of bioactive itaconates, and the preparation of an itaconate-based bio-orthogonal probe.

UR - http://www.scopus.com/inward/record.url?scp=85211454840&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85211454840&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.4c03514

DO - 10.1021/acs.orglett.4c03514

M3 - Article

AN - SCOPUS:85211454840

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Decarboxylative Coupling of Ketoacids with Allylic Acetates

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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