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The Reactivity of Enantiopure (S)-6-Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions

Abstract : Enantiopure N-benzyl 6-oxopipecolic acid, obtained from (S)-2-aminoadipic acid, was evaluated under π-cationic cyclization conditions. If the combination of SOCl2/AlCl3 seems to be superior in terms of the reaction yields, use of PPA, (CF3CO)2O/BF3·Et2O, and Eaton's reagent is also very interesting since in addition to the expected keto-lactam, reduced- and oxidized keto-lactam, enamides and enamidones containing CF3CO– residue are isolated. Mechanisms leading to these products as well as the ones resulting from their acidic treatment were proposed and discussed with the help, in some cases, of univocal transformations and X-ray analysis. © 2018 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02413282
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Submitted on : Monday, December 16, 2019 - 10:43:31 AM
Last modification on : Thursday, July 2, 2020 - 3:29:38 AM

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P. Šafář, Š. Marchalín, B. Balónová, M. Šoral, J. Moncol, et al.. The Reactivity of Enantiopure (S)-6-Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2018, 2018 (40), pp.5499-5511. ⟨10.1002/ejoc.201800908⟩. ⟨hal-02413282⟩

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