Visible-Light-Driven Synthesis of <i>N</i>-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and <i>In Situ</i> Generated Imines

One-pot, multicomponent reactions are known for their green and efficient nature. We report a novel three-component reaction of alkyl amines, alkyl glyoxylates, and unactivated alkyl bromides under visible-light-induced palladium catalysis, yielding <i>N</i>-alkyl unnatural α-amino acid derivatives. This method offers mild conditions, broad substrate scope, and excellent functional group tolerance without requiring stoichiometric organometallic reagents. The approach has promising applications in protein engineering and drug discovery.

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Publication Details

Journal
Organic Letters
Published
2024-09-23
DOI
https://doi.org/10.1021/acs.orglett.4c03297
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.42

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article

Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines

Chaoying Qiu, Ming Chen, Yan Jiang, Sen Yang et al.
2 citations
Organic Letters
Fluorine in Organic Chemistry
0.42
article

Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines

Chaoying Qiu, Ming Chen, Yan Jiang, Sen Yang, Hao Hu
article en
2 citations

Abstract

One-pot, multicomponent reactions are known for their green and efficient nature. We report a novel three-component reaction of alkyl amines, alkyl glyoxylates, and unactivated alkyl bromides under visible-light-induced palladium catalysis, yielding <i>N</i>-alkyl unnatural α-amino acid derivatives. This method offers mild conditions, broad substrate scope, and excellent functional group tolerance without requiring stoichiometric organometallic reagents. The approach has promising applications in protein engineering and drug discovery.

Organic LettersVol. 26(39)
Changzhou University (CN)
National Natural Science Foundation of China, Government of Jiangsu Province, Jiangsu Provincial Department of Education, Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department
Openalex Percentile: Top 42%
Fluorine in Organic Chemistry
0.42
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Visible-Light-Driven Synthesis of <i>N</i>-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and <i>In Situ</i> Generated Imines — Chaoying Qiu, Ming Chen, et al. · Organic Letters (2024) | TGRS Research Map | TGRS