A Lewis/Brønsted acid-mediated route to furans from nitroalkenes and enol ethers

A Lewis/Brønsted acid-mediated route to furans from nitroalkenes and enol ethers Full article

Journal

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

Output data

Year: 2025, Volume: 23, Number: 44, Pages: 10159-10167 Pages count : 9 DOI: 10.1039/d5ob01200g

Authors

Zhirov Alexander V. ^1,2 , Pospelov Evgeny V ² , Sukhorukov Alexey Yu. ²

Affiliations

1	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 1, str. 3, Moscow, 119991, Russian Federation.
2	Laboratory of Organic and Metal-Organic Nitrogen-Oxygen Systems (LOMONOS), N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, 119991, Russian Federation. sukhorukov@ioc.ac.ru.

A novel approach toward tri- and tetra-substituted furans via a Brønsted acid-mediated ring contraction of readily available 1,2-oxazine N-oxides is reported. This method provides a two-step route to obtain polysubstituted furans from simple feedstocks—nitroalkenes and enol ethers or ketals. An operationally simple procedure combining the synthesis of 1,2-oxazine N-oxides and their ring contraction in one pot was also developed. Mechanistic studies revealed that a Nef-type reaction pathway was involved in the ring contraction. The synthetic utility of the obtained furans was demonstrated by their conversion into diastereomerically pure tetrahydrofurans.

Zhirov A.V. , Pospelov E.V. , Sukhorukov A.Y.
A Lewis/Brønsted acid-mediated route to furans from nitroalkenes and enol ethers
Organic & Biomolecular Chemistry. 2025. V.23. N44. P.10159-10167. DOI: 10.1039/d5ob01200g WOS Scopus OpenAlex

Web of science:	WOS:001599317300001
Scopus:	2-s2.0-105021478073
OpenAlex:	W4415187781

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