Stereoselective synthesis of functionalized perhydropyrrolo[1,2- b ]isoxazoles based on (3 + 2)-annulation of donor–acceptor cyclopropanes and isoxazolines

Stereoselective synthesis of functionalized perhydropyrrolo[1,2- b ]isoxazoles based on (3 + 2)-annulation of donor–acceptor cyclopropanes and isoxazolines Full article

Journal

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

Output data

Year: 2026, Volume: 24, Number: 1, Pages: 207-215 Pages count : 9 DOI: 10.1039/d5ob01604e

Authors

Potapov Konstantin V. ¹ , Novikov Maxim A. ¹ , Kozmenko Yaroslav V. ^2,1 , Solyev Pavel N. ² , Volodin Alexander D. ³ , Korlyukov Alexander A. ³ , Novikov Roman A. ¹ , Tomilov Yury V. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia
2	Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences, 32 Vavilov St., Moscow 119991, Russia
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., Moscow, 119334, Russian Federation

Funding (1)

N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences

A stereoselective route to access substituted pyrrolidine cores via Lewis acid catalyzed (3 + 2)-annulation of donor–acceptor cyclopropanes (DACs) and isoxazolines has been developed. Exclusive cis-2,5-stereoselectivity was governed by kinetically controlled conditions using Sn(OTf)2 as the catalyst, while excellent trans-2,5-stereoselectivity was achieved by thermodynamically controlled conditions using Sc(OTf)3 as the catalyst. For DACs bearing electron-poor substituents, Yb(NTf2)3 proved to be the most efficient catalyst due to its higher Lewis acidity compared to triflates. The isoxazoline (3 + 2)-annulation reaction was also extended to bicyclo[1.1.0]butanes (BCBs), providing easy access to the 2-azabicyclo[2.1.1]hexane core, which may be considered as a promising 3D-bioisosteric replacement for pyrrole and pyrrolidine motifs.

Potapov K.V. , Novikov M.A. , Kozmenko Y.V. , Solyev P.N. , Volodin A.D. , Korlyukov A.A. , Novikov R.A. , Tomilov Y.V.
Stereoselective synthesis of functionalized perhydropyrrolo[1,2- b ]isoxazoles based on (3 + 2)-annulation of donor–acceptor cyclopropanes and isoxazolines
Organic and Biomolecular Chemistry. 2026. V.24. N1. P.207-215. DOI: 10.1039/d5ob01604e WOS Scopus OpenAlex

Web of science:	WOS:001631382700001
Scopus:	2-s2.0-105023841662
OpenAlex:	W4416736238

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