Extended Version of the Corey–Chaykovsky Reaction: Synthesis of 2,4-Substituted Furans by the Treatment of β-Dialkylamino Chalcones with Dimethylsulfonium Methylide

Extended Version of the Corey–Chaykovsky Reaction: Synthesis of 2,4-Substituted Furans by the Treatment of β-Dialkylamino Chalcones with Dimethylsulfonium Methylide Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2023, Volume: 88, Number: 13, Pages: 8227-8235 Pages count : 9 DOI: 10.1021/acs.joc.3c00203

Authors

Shcherbakov Roman O. ¹ , Myasnikov Danil A. ¹ , Trushkov Igor V. ^2,3 , Uchuskin Maxim G. ¹

Affiliations

1	Department of Chemistry, Perm State University, Bukireva st. 15, Perm 614990, Russia
2	D. Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela St. 1, Moscow 117997, Russia
3	N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia

We describe the synthesis of functionalized furans using the concept of the extended Corey–Chaykovsky reaction. Namely, β,β-disubstituted α,β-unsaturated ketones were treated with dimethylsulfonium methylide to give vinyloxiranes, which immediately rearranged into the corresponding furans. The developed approach allows for synthesizing a broad range of unsymmetrically di- and trisubstituted furans containing various functionalities in the core.

Shcherbakov R.O. , Myasnikov D.A. , Trushkov I.V. , Uchuskin M.G.
Extended Version of the Corey–Chaykovsky Reaction: Synthesis of 2,4-Substituted Furans by the Treatment of β-Dialkylamino Chalcones with Dimethylsulfonium Methylide
Journal of Organic Chemistry. 2023. V.88. N13. P.8227-8235. DOI: 10.1021/acs.joc.3c00203 WOS Scopus OpenAlex

Web of science:	WOS:001008102400001
Scopus:	2-s2.0-85163365740
OpenAlex:	W4379093974

DB	Citing
OpenAlex	16
Scopus	14
Web of science	14