Pd-Catalyzed Asymmetric Allylic Alkylation of Carboxylic Acids for the Synthesis of Chiral Butenolidyl Ester Prodrugs and Peptide–Drug Conjugates

A Pd-catalyzed asymmetric allylic alkylation of γ-OBoc-butenolides with carboxylic acids enables the direct synthesis of chiral γ-substituted butenolides under mild conditions. The reaction proceeds with broad substrate scope and excellent stereocontrol, tolerating diverse carboxylic acids including those derived from natural products, pharmaceuticals, and peptides. The resulting chiral butenolidyl esters serve as valuable prodrug scaffolds and peptide-drug conjugation units, offering a new asymmetric strategy for the construction of stereodefined bioconjugates and chiral prodrugs.

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Publication Details

Journal
Organic Letters
Published
2025-11-27
DOI
https://doi.org/10.1021/acs.orglett.5c04479
Citations
2
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
1.87
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article

Pd-Catalyzed Asymmetric Allylic Alkylation of Carboxylic Acids for the Synthesis of Chiral Butenolidyl Ester Prodrugs and Peptide–Drug Conjugates

Gui-Qing Xu, Duanyang Kong, Wenfei Ren, Yue Ma et al.
2 citations
Organic Letters
Asymmetric Synthesis and Catalysis
1.87
article

Pd-Catalyzed Asymmetric Allylic Alkylation of Carboxylic Acids for the Synthesis of Chiral Butenolidyl Ester Prodrugs and Peptide–Drug Conjugates

Gui-Qing Xu, Duanyang Kong, Wenfei Ren, Yue Ma, Chunshan Song
article en
2 citations

Abstract

A Pd-catalyzed asymmetric allylic alkylation of γ-OBoc-butenolides with carboxylic acids enables the direct synthesis of chiral γ-substituted butenolides under mild conditions. The reaction proceeds with broad substrate scope and excellent stereocontrol, tolerating diverse carboxylic acids including those derived from natural products, pharmaceuticals, and peptides. The resulting chiral butenolidyl esters serve as valuable prodrug scaffolds and peptide-drug conjugation units, offering a new asymmetric strategy for the construction of stereodefined bioconjugates and chiral prodrugs.

Organic LettersVol. 27(49)
State Key Laboratory of Chemical Engineering (CN), Beijing University of Chemical Technology (CN), Henan Normal University (CN)
Openalex Percentile: Top 13%
Asymmetric Synthesis and Catalysis
1.87
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