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Updated: Aug 27, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Electrocatalytic Polarity Inversion of Azlactones: Access to α-Quaternary Amino Acids with Electron-Rich SOMOphiles
Paula Rodríguez1, David Buedo1, Alberto Vega-Peñaloza1
1Section of Organic Chemistry, Department of Inorganic and Organic Chemistry, University of Barcelona, Barcelona, Spain.
Abstract:
The use of azlactones as nucleophiles is a well-established strategy to access α-quaternary amino acids. Herein, we present an electrocatalytic approach that reverses the natural polarity of azlactones. Indirect oxidation of the azlactone enolate, using triarylamine electrocatalysts, generates an electrophilic radical intermediate that couples with a variety of electron-rich SOMOphiles. This strategy enables Csp3─Csp2 and Csp3─Csp3 bond formation at the α-position of the azlactone, providing access to arylated, β-oxoalkylated, alkenylated, and allylated quaternary amino acid derivatives.
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