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Diastereoselective synthesis of atropisomeric pyrazolyl pyrrolo[3,4-d]isoxazolidines via pyrazolyl nitrone cycloaddition to facially divergent maleimides: intensive NMR and DFT studies

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Abstract

A pyrazolyl nitrone (2) underwent 1,3-dipolar cycloadditions to afford some N-substituted maleimides (3a–o). An atropisomeric character was introduced into the formed cycloadducts by using maleimides that have a restricted rotation around the C–N bond. Also, facial selectivity of both endo and exo cycloaddition was observed where the major atropisomer was one that is formed by attacking the nitrone from the less hindered face of the dipolarophile. On the other hand, maleimides with free rotation around the C–N bond led to endo and exo cycloadducts without atropisomerism. The presence of atropisomerism in the formed cycloadducts was confirmed by extensive NMR studies and DFT calculations.

Graphical abstract: Diastereoselective synthesis of atropisomeric pyrazolyl pyrrolo[3,4-d]isoxazolidines via pyrazolyl nitrone cycloaddition to facially divergent maleimides: intensive NMR and DFT studies

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Article information


Submitted
30 Nov 2019
Accepted
16 Dec 2019
First published
06 Jan 2020

This article is Open Access

RSC Adv., 2020,10, 845-850
Article type
Paper

Diastereoselective synthesis of atropisomeric pyrazolyl pyrrolo[3,4-d]isoxazolidines via pyrazolyl nitrone cycloaddition to facially divergent maleimides: intensive NMR and DFT studies

A. I. Said and T. I. El-Emary, RSC Adv., 2020, 10, 845
DOI: 10.1039/C9RA10039C

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