Issue 18, 2022

Electrochemical enantioselective dihydroxylation reaction of N-alkenyl nucleobases for the construction of chiral acyclic nucleosides

Abstract

A simple and sustainable KI-mediated electrochemical enantioselective dihydroxylation reaction of N-alkenyl nucleobases was developed for the first time in an undivided cell. A series of chiral acyclic nucleosides bearing two adjacent hydroxyl groups and stereogenic carbon centers in the corresponding side chain were obtained in up to 97% yield and 98% ee with only a 0.1 mol% Os catalyst. Moreover, this reaction featuring a high TON (up to 950) and exogenous oxidant-free conditions provides an efficient and environmentally benign synthetic route to chiral acyclic nucleosides.

Graphical abstract: Electrochemical enantioselective dihydroxylation reaction of N-alkenyl nucleobases for the construction of chiral acyclic nucleosides

Supplementary files

Article information

Article type
Research Article
Submitted
17 jun 2022
Accepted
29 jul 2022
First published
30 jul 2022

Org. Chem. Front., 2022,9, 4818-4822

Electrochemical enantioselective dihydroxylation reaction of N-alkenyl nucleobases for the construction of chiral acyclic nucleosides

Q. Zhang, P. Lu, S. Wang, L. Li, G. Qu and H. Guo, Org. Chem. Front., 2022, 9, 4818 DOI: 10.1039/D2QO00971D

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