Issue 26, 2022

Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones

Abstract

6-Methylene-5-oxaspiro[2.4]heptanones have been synthesized via base-catalyzed dimerization of available alkynyl cyclopropyl ketones. The reaction proceeds effectively in the presence of the t-BuOK/t-BuOH/THF catalytic system at room temperature to afford the desired spirocycles in a regio- and stereoselective manner. A wider synthetic utility of alkynyl cyclopropyl ketones as novel building blocks was demonstrated by the synthesis of diverse spirocyclopropanes.

Graphical abstract: Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones

Supplementary files

Article information

Article type
Paper
Submitted
05 May 2022
Accepted
15 Jun 2022
First published
15 Jun 2022

Org. Biomol. Chem., 2022,20, 5325-5333

Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones

S. O. Samultceva, M. Yu. Dvorko, D. A. Shabalin, I. A. Ushakov, A. V. Vashchenko, E. Yu. Schmidt and B. A. Trofimov, Org. Biomol. Chem., 2022, 20, 5325 DOI: 10.1039/D2OB00854H

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