Initial Examinations of the Diastereoselectivity and Chemoselectivity of the Intramolecular Silyl Nitronate Cycloadditions with Alkenyl/Alkynyl Nitroethers

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This paper examined the chemoselectivity and diastereoslectivity of silyl nitronate alkenyn-nitroethers in Intramolecular Silyl Nitronate Cycloadditions (ISNC) to produce isoxazole derivatives with interesting medicinal properties. These reactions resulted in the formation of either dihydrofuro[3,4-c]isoxazolines/isoxazolidines and/or alkynyl moieties attached to 2,5-dihydrofuryl carbonyls. It also discerned the diastereoselectivity of the resulting cyclic adducts and compared those to previous findings. The reactions were also investigated with Spartan molecular modeling computations to aide in the understanding of any displayed chemo- and/or stereoselectivity. These [3+2]-cycloaddition reactions demonstrated excellent to complete chemospecificity. The cycloadditions also demonstrated remarkable diastereospecificity in that each diastereomer of the nitroethers resulted in the formation of only one of four possible diastereomeric outcomes. The stereochemistry of the major diastereomers did not agree with previously published findings.

Ce résumé expose les affirmations des auteurs. BNTIC ne l’interprète pas comme une validation indépendante des résultats.