Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles

Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles Full article

Journal

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

Output data

Year: 2021, Volume: 19, Number: 15, Pages: 3413-3427 Pages count : 15 DOI: 10.1039/d1ob00146a

Authors

Motornov Vladimir A. ¹ , Tabolin Andrey A. ¹ , Nelyubina Yulia V. ² , Nenajdenko Valentine G. ³ , Ioffe Sema L. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, Russia
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow, Russia
3	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia

An efficient route for the synthesis of multifunctionalized pyrrolidines based on copper-catalyzed diastereoselective [3 + 2]-cycloaddition of nitroalkenes with azomethine ylides was developed. Novel fluorinated heterocycles – β-fluoro-β-nitropyrrolidines – were accessed via this method. The products can be prepared in good to excellent yields and with high diastereoselectivity. Subsequent transformations of pyrrolidines including oxidative aromatization into fluorinated pyrrolines and medicinally attractive β-fluoro-NH-pyrroles as well as chemoselective reduction reactions were demonstrated. Application of the developed procedures for the non-fluorinated analogues was demonstrated to lead to various β-substituted pyrrole derivatives.

Motornov V.A. , Tabolin A.A. , Nelyubina Y.V. , Nenajdenko V.G. , Ioffe S.L.
Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles
Organic & Biomolecular Chemistry. 2021. V.19. N15. P.3413-3427. DOI: 10.1039/d1ob00146a WOS Scopus OpenAlex

≡ Web of science:	WOS:000632567000001
≡ Scopus:	2-s2.0-85104897641
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