Synlett
DOI: 10.1055/a-2627-8548
Letter

Lewis Acid-Catalyzed Cyanomethylation of α,β-Unsaturated Keto Esters and Activated Ketones Using Vinyl Azide as an Acetonitrile Equivalent

Xudong Zhang
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China
,
Min Yang
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China
,
Jian Xiao
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China
,
Bin Chen
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China
,
Minghui Hui Xu
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China
,
Bin-Qin Wang
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China
,
Ping Hu
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China
,
Peng Cao
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China
› Author Affiliations

Supported by: Sichuan Science and Technology Program 2022JDJQ0013,2022NSFSC1232
Supported by: National Natural Science Foundation of China 2022JDJQ0013,2022NSFSC1232


Preview

Abstract

Lewis acid-catalyzed cyanomethylation reactions of α,β-unsaturated ketoesters and ketoamides with α-isopropanol vinyl azide were reported. The corresponding cyanoalkylated products were obtained in 40–97% and 45–96% yields, respectively, through 1,4- and 1,2-addition pathways.

Supplementary Material



Publication History

Received: 08 May 2025

Accepted after revision: 04 June 2025

Accepted Manuscript online:
04 June 2025

Article published online:
24 July 2025

© 2025. Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany