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2-Vinyl Threoninol Derivatives via Acid-Catalyzed Allylic Substitution of Bisimidates

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Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, Latvia LV 1006
Cite this: J. Org. Chem. 2015, 80, 11, 5934–5943
Publication Date (Web):May 5, 2015
https://doi.org/10.1021/acs.joc.5b00529
Copyright © 2015 American Chemical Society

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    Abstract

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    A diastereoselective synthesis of 4-vinyl oxazolines syn-2 was developed based on an acid-catalyzed cyclization of bistrichloroacetimidates (E)-1. The reaction likely involves an allyl carbenium ion intermediate in which the adjacent stereocenter directs the stereoselectivity for C–N bond formation. Oxazolines syn-2 were transformed to C-quaternary threoninol, threoninal, and threonine derivatives which can be further incorporated into complex natural compounds.

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    Supporting Information

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    ORTEP diagram for compound 10. Complete set of results for the imidate 1 cyclization studies. Copies of 1H NMR, 13C NMR, and 2D spectra for compounds 114. Copies of chiral HPLC chromatograms for compounds (S)-4a and S,S-10. The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.5b00529.

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    Cited By

    This article is cited by 7 publications.

    1. Aleix Rodríguez, Xavier Ariza, Miguel A. Contreras, Jordi Garcia, Paul Lloyd-Williams, Nerea Mercadal, and Carolina Sánchez . A Useful Allene for the Stereoselective Synthesis of Protected Quaternary 2-Amino-2-vinyl-1,3-diols. The Journal of Organic Chemistry 2017, 82 (3) , 1851-1855. https://doi.org/10.1021/acs.joc.6b02765
    2. Aleksandra Narczyk, Sebastian Stecko. The synthesis of unnatural α-alkyl- and α-aryl-substituted serine derivatives. Organic & Biomolecular Chemistry 2020, 18 (6) , 1204-1213. https://doi.org/10.1039/C9OB02472G
    3. Masahiro Shimizu, Jun Kikuchi, Azusa Kondoh, Masahiro Terada. Chiral Brønsted acid-catalyzed intramolecular S N 2′ reaction for enantioselective construction of a quaternary stereogenic center. Chemical Science 2018, 9 (26) , 5747-5757. https://doi.org/10.1039/C8SC01942H
    4. Kouichi Matsumoto, Jun-ichi Yoshida, Yu Miyamoto, Naoya Mitani, Rina Yanagi, Shigenori Kashimura, Seiji Suga. Synthesis of Oxazolines from N-Allylamides Using an Electrochemically Generated ArS(ArSSAr)+ Pool. HETEROCYCLES 2018, 96 (8) , 1373. https://doi.org/10.3987/COM-18-13942
    5. M. Skvorcova, A. Jirgensons. Intramolecular cyclopropylmethylation via non-classical carbocations. Organic & Biomolecular Chemistry 2017, 15 (33) , 6909-6912. https://doi.org/10.1039/C7OB01721A
    6. Jekaterina Sirotkina, Liene Grigorjeva, Aigars Jirgensons. Synthesis of Alkynyl‐Glycinols by Lewis Acid Catalyzed Propargylic Substitution of Bis‐Imidates. European Journal of Organic Chemistry 2015, 2015 (31) , 6900-6908. https://doi.org/10.1002/ejoc.201500937
    7. Varun Kumar, Kristine Klimovica, Dace Rasina, Aigars Jirgensons. ChemInform Abstract: 2‐Vinyl Threoninol Derivatives via Acid‐Catalyzed Allylic Substitution of Bisimidates.. ChemInform 2015, 46 (43) https://doi.org/10.1002/chin.201543139

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