Sequential Formal [4+1]‐Cycloaddition, C−H Functionalization and Suzuki–Miyaura Cross‐Coupling for the Synthesis of Trisubstituted Isoxazolines

Sequential Formal [4+1]‐Cycloaddition, C−H Functionalization and Suzuki–Miyaura Cross‐Coupling for the Synthesis of Trisubstituted Isoxazolines Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2021, Volume: 2021, Number: 18, Pages: 2680-2693 Pages count : 14 DOI: 10.1002/ejoc.202100313

Authors

Ushakov Pavel Yu. ^1,2 , Sukhorukov Alexey Yu. ^2,3 , Ioffe Sema L. ² , Tabolin Andrey A. ²

Affiliations

1	Department of Chemistry M. V. Lomonosov Moscow State University Leninskie gory, 1, str. 3 119991 Moscow Russia
2	Laboratory of organic and metal-organic nitrogen-oxygen systems N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences Leninsky prospect, 47 119991 Moscow Russia
3	Plekhanov Russian University of Economics Stremyanny per. 36 117997 Moscow Russia

Suzuki–Miyaura cross-coupling reaction of 3-bromomethyl isoxazolines with arylboronic acids was suggested as final C−C bond forming step in convenient diastereoselective route to trisubstituted isoxazolines. The required bromides were readily available from nitroalkenes and sulfonium ylides through an efficient sequence of formal [4+1]-cycloaddition and C−H functionalization of intermediate isoxazoline N-oxides. The synthetic utility of the obtained isoxazolines was demonstrated by their conversion into valuable products such as hydroxy ketone, pyrrolidinone, etc.

Ushakov P.Y. , Sukhorukov A.Y. , Ioffe S.L. , Tabolin A.A.
Sequential Formal [4+1]‐Cycloaddition, C−H Functionalization and Suzuki–Miyaura Cross‐Coupling for the Synthesis of Trisubstituted Isoxazolines
European Journal of Organic Chemistry. 2021. V.2021. N18. P.2680-2693. DOI: 10.1002/ejoc.202100313 WOS Scopus OpenAlex

Web of science:	WOS:000664253200010
Scopus:	2-s2.0-85108258091
OpenAlex:	W3148913616

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OpenAlex	9
Scopus	9
Web of science	9