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

Konstantin V. Potapov; Maxim A. Novikov; Yaroslav V. Kozmenko; Pavel N Solyev; Alexander D. Volodin; Alexander Korlyukov; Roman A. Novikov; Yury Tomilov

doi:10.1039/d5ob01604e

January 1, 2025Organic & Biomolecular Chemistry

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

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Key Points

Synthesis yields exclusive cis-2,5-stereoselectivity under kinetically-controlled conditions,
Donor-acceptor cyclopropanes are used in the synthesis of functionalized isoxazoles with high efficiency.
Catalyzed reactions utilizing Sn(OTf)2 form a novel pathway for creating complex molecular structures.
The findings highlight the potential of this method for developing advanced functional materials.

Implication

Stereoselective synthesis creates substituted pyrrolidine in isoxazolines, suggesting effective use of Lewis acid catalysis.

Abstract

A Stereoselective route to substituted pyrrolidine core via Lewis acid catalyzed (3+2)-annulation of donor-acceptor cyclopropanes (DAC) to isoxazolines was developed. Exclusive cis -2,5-stereoselectivity was governed by kinetically-controlled conditions using Sn(OTf) 2 as...

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Cite This Study

Potapov et al. (2025) studied this question.

synapsesocial.com/papers/692b9d831d383f2b2a3797fb https://doi.org/10.1039/d5ob01604e

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

Key Points

Implication

Abstract

Discussion

Cite This Study

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

Key Points

Implication

Abstract

Discussion

Cite This Study

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