Site‑, enantio‑ and stereo‑selectivities of the 1,3‑dipolar cycloaddition reactions of oxanorbornadiene with C,N‑disubstituted nitrones and dimethyl nitrilimines: a DFT mechanistic study

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dc.contributor.authorOpoku, Ernest
dc.contributor.authorArhin, Grace
dc.contributor.authorPipim, George Baffour
dc.contributor.authorAdams, Anita Houston
dc.contributor.authorTia, Richard
dc.contributor.authoret. al
dc.date.accessioned2020-07-08T11:46:11Z
dc.date.accessioned2023-04-19T02:06:39Z
dc.date.available2020-07-08T11:46:11Z
dc.date.available2023-04-19T02:06:39Z
dc.date.issued2020-01-01
dc.descriptionAn article published by Springer-Verlag GmbH Germany and also available at https://doi.org/10.1007/s00214-019-2529-8en_US
dc.description.abstract1,3-Dipolar cycloaddition of nitrones to oxanorbornadienes is an important method for the enantioselective synthesis of highly substituted 5-membered heterocycles such as furans and isoxazolidines, which have high utility in the chemical and pharmaceutical industries. The mechanism of the reaction and the effects of substituents on the (3 + 2) cycloaddition reactions (32CA) of C,N-dialkyl nitrones with a series of substituted oxanorbornadienes have been studied with focus on the site-selectivity (attack on the more substituted double bond of the oxanorbornadiene derivatives versus attack on the less substituted double bond), enantioselectivity and stereo-selectivity using density functional theory calculations at the M06/6-311++G(d,p) of theory. The results showed that the addition step to form the bicyclic isoxazolidines cycloadducts has generally low barriers compared to the cycloreversion step which converts the cycloadducts into furans and monocyclic isoxazolidines. Generally, electron-withdrawing substituents favour the nitrone attack on the highly substituted double bond, while electron-donating substituents favour the attack on less substituted double bond. The R enantiomers are generally favoured over the S enantiomers, and exo stereo-isomers are generally favoured over the endo stereo-isomers, irrespective of substituents.en_US
dc.description.sponsorshipKNUSTen_US
dc.identifier.citationTheoretical Chemistry Accounts (2020) 139:16 https://doi.org/10.1007/s00214-019-2529-8en_US
dc.identifier.urihttps://ir.knust.edu.gh/handle/123456789/12659
dc.language.isoenen_US
dc.publisherSpringer-Verlag GmbH Germanyen_US
dc.subjectDipoleen_US
dc.subjectOxanorbornadieneen_US
dc.subjectNitroneen_US
dc.subjectEnantioselectivityen_US
dc.subjectDensity functional theoryen_US
dc.titleSite‑, enantio‑ and stereo‑selectivities of the 1,3‑dipolar cycloaddition reactions of oxanorbornadiene with C,N‑disubstituted nitrones and dimethyl nitrilimines: a DFT mechanistic studyen_US
dc.typeArticleen_US
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