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Polymer-Supported Stereoselective Synthesis of Tetrahydrobenzopyrazino-thiadiazinone Dioxides via N-Sulfonyl Iminiums
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    Polymer-Supported Stereoselective Synthesis of Tetrahydrobenzopyrazino-thiadiazinone Dioxides via N-Sulfonyl Iminiums
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    Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University, 17 Listopadu 12, 771 46 Olomouc, Czech Republic
    Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, Indiana 46556, United States
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    ACS Combinatorial Science

    Cite this: ACS Comb. Sci. 2014, 16, 6, 293–302
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    https://doi.org/10.1021/co5000163
    Published February 27, 2014
    Copyright © 2014 American Chemical Society

    Abstract

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    The stereoselective synthesis of 1,2,11,11a-tetrahydrobenzo[e]pyrazino[1,2-b][1,2,4]thiadiazin-3(4H)-one 6,6-dioxides on a solid support via tandem N-sulfonyl iminium ion cyclization, followed by nucleophilic addition is reported. The synthesis proceeded with full control of stereoselectivity at the newly formed asymmetric carbon, under mild conditions, and using commercially available building blocks. The synthetic route provided high-purity crude products.

    Copyright © 2014 American Chemical Society

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    Details of the experimental procedures and the NMR spectra associated with this article. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 16 publications.

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    14. Pilar Ventosa-Andrés, Carlos Alfonso Barea Ripoll, Agustina La-Venia, Viktor Krchňák. Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization–nucleophilic addition. Tetrahedron Letters 2015, 56 (40) , 5424-5428. https://doi.org/10.1016/j.tetlet.2015.08.015
    15. Veronika Fülöpová, Petr Funk, Igor Popa, Claire McMaster, Miroslav Soural. Solid‐Phase Synthesis of Trisubstituted Benzo[ f ][1,2,3]triazolo[1,5‐ a ][1,4]diazepin‐6(5 H )‐ones and Their Sulfonyl Analogues under Mild Reaction Conditions. European Journal of Organic Chemistry 2015, 2015 (16) , 3551-3557. https://doi.org/10.1002/ejoc.201500314
    16. N.K. Terrett. Combinatorial Chemistry Online Volume 16, Issue 8, August 2014. Combinatorial Chemistry - an Online Journal 2014, 16 (8) , 29-31. https://doi.org/10.1016/j.comche.2014.06.002
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    ACS Combinatorial Science

    Cite this: ACS Comb. Sci. 2014, 16, 6, 293–302
    Click to copy citationCitation copied!
    https://doi.org/10.1021/co5000163
    Published February 27, 2014
    Copyright © 2014 American Chemical Society

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