Issue 2, 2024

Base-mediated trimerization of enones under solvent-free and ball-milling conditions

Abstract

An efficient mechanochemical trimerization of enones with KOtBu as the base and water as the proton source under solvent-free and ambient conditions has been developed. This protocol provides novel, simple, rapid and scalable access to 1,3,5-triaryl-2,4-acyl-cyclohexanols, which exist as chair conformations with all bulky substituents located at equatorial positions. In addition, the formed cyclohexanol derivatives can be further dehydrated to afford the corresponding cyclohexene derivatives with β,γ-unsaturation. By changing the type or amount of the employed base, another type of stereoisomer, where the 4-acyl group is situated at the axial position, can be favorably generated as the major product.

Graphical abstract: Base-mediated trimerization of enones under solvent-free and ball-milling conditions

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Article information

Article type
Paper
Submitted
31 Oct 2023
Accepted
15 Dec 2023
First published
29 Jan 2024
This article is Open Access
Creative Commons BY license

RSC Mechanochem., 2024,1, 162-166

Base-mediated trimerization of enones under solvent-free and ball-milling conditions

G. Shao, P. Li, Z. Yin, J. Chen, X. Xia and G. Wang, RSC Mechanochem., 2024, 1, 162 DOI: 10.1039/D3MR00010A

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