Issue 13, 2023

B(C6F5)3-catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes

Abstract

Spirocyclopropane-oxindoles are key motifs in biologically active compounds and are versatile synthetic intermediates. Herein, we report a metal-free, B(C6F5)3 catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes. This provides 25 variants of spirocyclopropane-oxindole derivatives. These spirocyclopropane-oxindole products were obtained in good to excellent yields (up to 99%) and high diastereoselectivities (up to 20 : 1 d.r.) under mild reaction conditions and could be performed on a gram scale.

Graphical abstract: B(C6F5)3-catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes

Supplementary files

Article information

Article type
Communication
Submitted
10 12月 2022
Accepted
18 1月 2023
First published
18 1月 2023

Chem. Commun., 2023,59, 1833-1836

B(C6F5)3-catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes

L. Xiao, L. Jin, Y. Zhao, J. Guo and D. W. Stephan, Chem. Commun., 2023, 59, 1833 DOI: 10.1039/D2CC06744G

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