Enantioselective Electrocatalytic Nitroalkylation

Juan Li; Jin Song; Chang Guo

doi:10.1055/a-2535-0710

Synlett, Table of Contents

Synlett 2025; 36(10): 1305-1309
DOI: 10.1055/a-2535-0710

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Enantioselective Electrocatalytic Nitroalkylation

Juan Li

^aInstitutes of Physical Science and Information Technology, Anhui University, Hefei, 230601, P. R. of China

,

Jin Song∗

^aInstitutes of Physical Science and Information Technology, Anhui University, Hefei, 230601, P. R. of China

,

Chang Guo∗

^bHefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China

› Author Affiliations

Abstract

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Abstract

Asymmetric electrocatalytic processes hold great promise for the sustainable synthesis of chiral compounds. However, maintaining stereochemical control during the anodic oxidative cross-dehydrogenative coupling of different nucleophiles poses significant challenges. To address this, a novel electrocatalytic strategy has been developed that achieves an enantioconvergent nitroalkylation between benzoxazolyl esters and nitroalkanes via radical pathways. This method produces enantioenriched nitro esters without the need for additional stoichiometric chemical oxidants. Mechanistic studies have revealed that the nickel catalyst plays a critical role in both the electrochemical activation and the determination of stereoselectivity. This approach facilitates transformations that are challenging under thermal conditions, including umpolung reactivity, the formation of quaternary carbon centers, and remote enantiocontrol.

Key words

electrocatalysis - radical reaction - nickel catalysis - enantioselectivity - cross-dehydrogenative coupling - nitroalkylation

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References

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