Iron‐Catalyzed Stereoselective C–H Acylation of 2‐Acetamido Acrylates

An iron‐catalyzed oxidative acylation of acylamido acrylates with abundant aldehydes has been developed. The use of mono N‐protected amino acids results in the unusual assembly of α,β ‐unsaturated compounds in a predictable (Z)‐stereoselective fashion, thereby offering a complementary tool toward the synthesis of unnatural γ ‐carbonyl α‐amino acid derivatives. Density functional theory studies provide insights into the stereodetermining step of the radical reaction pathway.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2025-09-19
DOI
https://doi.org/10.1002/adsc.70047
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Iron‐Catalyzed Stereoselective C–H Acylation of 2‐Acetamido Acrylates

Thanh V. Q. Nguyen, Werngard Czechtizky, Enrique Gómez‐Bengoa, C. Kyriacou et al.
Advanced Synthesis & Catalysis
Catalytic C–H Functionalization Methods
article

Iron‐Catalyzed Stereoselective C–H Acylation of 2‐Acetamido Acrylates

Thanh V. Q. Nguyen, Werngard Czechtizky, Enrique Gómez‐Bengoa, C. Kyriacou, Arkaitz Correa
article en

Abstract

An iron‐catalyzed oxidative acylation of acylamido acrylates with abundant aldehydes has been developed. The use of mono N‐protected amino acids results in the unusual assembly of α,β ‐unsaturated compounds in a predictable (Z)‐stereoselective fashion, thereby offering a complementary tool toward the synthesis of unnatural γ ‐carbonyl α‐amino acid derivatives. Density functional theory studies provide insights into the stereodetermining step of the radical reaction pathway.

Advanced Synthesis & CatalysisVol. 367(18)
University of the Basque Country (ES), AstraZeneca (Netherlands) (NL), AstraZeneca (Sweden) (SE)
European Commission, Eusko Jaurlaritza, Euskal Herriko Unibertsitatea, European Regional Development Fund, European Social Fund
Openalex Percentile: Top 81%
Catalytic C–H Functionalization Methods
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