Base-controlled divergent oxidative dimerization of allomaltol-containing enolates: access to distinct diastereomers of 1,4-diketones

Base-controlled divergent oxidative dimerization of allomaltol-containing enolates: access to distinct diastereomers of 1,4-diketones Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2026, DOI: 10.1039/d6ob00932h

Authors

Komogortsev Andrey N. ¹ , Milyutin Constantine V. ^1,2 , Kuzmina Anna G. ^1,2

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation
2	National Research University Higher School of Economics, 101000 Moscow, Russia

In the present communication, a novel synthetic approach to allomaltol-containing 1,4-diketones has been developed. The strategy relies on oxidative enolate coupling of the corresponding ketones and enables diastereodivergent synthesis controlled by the nature of the base. Depending on the base employed, two distinct diastereomers (meso and racemic forms) are selectively obtained from the same starting material. Their interconversion under various conditions was demonstrated, indicating thermodynamic control of the stereochemical outcome. The structures of both diastereomers were unambiguously established via X-ray analysis. Furthermore, the synthesized 1,4-diketones serve as versatile precursors for a series of novel tetrasubstituted furan derivatives

Komogortsev A.N. , Milyutin C.V. , Kuzmina A.G.
Base-controlled divergent oxidative dimerization of allomaltol-containing enolates: access to distinct diastereomers of 1,4-diketones
Organic & Biomolecular Chemistry. 2026. DOI: 10.1039/d6ob00932h WOS OpenAlex

Submitted:	Jun 17, 2026
Accepted:	Aug 27, 2026
Published print:	Sep 8, 2026
Published online:	Sep 8, 2026

≡ Web of science:	WOS:001869496700001
≡ OpenAlex:	W7211940529