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Initial Examinations of the Diastereoselectivity and Chemoselectivity of the Intramolecular Silyl Nitronate Cycloadditions with Alkenyl/Alkynyl Nitroethers
Version 1
: Received: 22 October 2024 / Approved: 23 October 2024 / Online: 24 October 2024 (08:01:20 CEST)
How to cite:
Stevens, K.; Li, S. K.; Kaufman, E.; Schull, A.; Hassebroek, K.; Stevens, J.; Grandbois, M.; Viste, A.; Duffy-Matzner, J. Initial Examinations of the Diastereoselectivity and Chemoselectivity of the Intramolecular Silyl Nitronate Cycloadditions with Alkenyl/Alkynyl Nitroethers. Preprints2024, 2024101840. https://doi.org/10.20944/preprints202410.1840.v1
Stevens, K.; Li, S. K.; Kaufman, E.; Schull, A.; Hassebroek, K.; Stevens, J.; Grandbois, M.; Viste, A.; Duffy-Matzner, J. Initial Examinations of the Diastereoselectivity and Chemoselectivity of the Intramolecular Silyl Nitronate Cycloadditions with Alkenyl/Alkynyl Nitroethers. Preprints 2024, 2024101840. https://doi.org/10.20944/preprints202410.1840.v1
Stevens, K.; Li, S. K.; Kaufman, E.; Schull, A.; Hassebroek, K.; Stevens, J.; Grandbois, M.; Viste, A.; Duffy-Matzner, J. Initial Examinations of the Diastereoselectivity and Chemoselectivity of the Intramolecular Silyl Nitronate Cycloadditions with Alkenyl/Alkynyl Nitroethers. Preprints2024, 2024101840. https://doi.org/10.20944/preprints202410.1840.v1
APA Style
Stevens, K., Li, S. K., Kaufman, E., Schull, A., Hassebroek, K., Stevens, J., Grandbois, M., Viste, A., & Duffy-Matzner, J. (2024). Initial Examinations of the Diastereoselectivity and Chemoselectivity of the Intramolecular Silyl Nitronate Cycloadditions with Alkenyl/Alkynyl Nitroethers. Preprints. https://doi.org/10.20944/preprints202410.1840.v1
Chicago/Turabian Style
Stevens, K., Arlen Viste and Jetty Duffy-Matzner. 2024 "Initial Examinations of the Diastereoselectivity and Chemoselectivity of the Intramolecular Silyl Nitronate Cycloadditions with Alkenyl/Alkynyl Nitroethers" Preprints. https://doi.org/10.20944/preprints202410.1840.v1
Abstract
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.
Chemistry and Materials Science, Organic Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
