Synthesis of chiral α-alkynyl-α-hydroxyamides by enantioselective alkynylation of α-keto amides

The α-hydroxyamide moiety is an important structural component in a wide variety of biologically active compounds and natural products. Herein, we describe a highly efficient and practical approach towards chiral quaternary α-alkynyl-α-hydroxyamides by Me<sub>2</sub>Zn-mediated addition of terminal alkynes to α-keto amides. The desired products are obtained in good yields and enantioselectivities with broad substrate and reagent scopes.

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Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01546d
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis of chiral α-alkynyl-α-hydroxyamides by enantioselective alkynylation of α-keto amides

Celia Andrés, Javier Nieto, Elena Prieto
Organic & Biomolecular Chemistry
Catalytic C–H Functionalization Methods
article

Synthesis of chiral α-alkynyl-α-hydroxyamides by enantioselective alkynylation of α-keto amides

Celia Andrés, Javier Nieto, Elena Prieto
article en

Abstract

The α-hydroxyamide moiety is an important structural component in a wide variety of biologically active compounds and natural products. Herein, we describe a highly efficient and practical approach towards chiral quaternary α-alkynyl-α-hydroxyamides by Me<sub>2</sub>Zn-mediated addition of terminal alkynes to α-keto amides. The desired products are obtained in good yields and enantioselectivities with broad substrate and reagent scopes.

Organic & Biomolecular ChemistryVol. 23(46)
Universidad de Valladolid (ES)
Junta de Castilla y León
Openalex Percentile: Top 76%
Catalytic C–H Functionalization Methods
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