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Novel Hybrid Prins/Aza-Prins Oxocarbenium/N-Acyliminium Cascade Expedient Access to Complex Indolizidines

Abstract : Heavy silyl enol ethers (mostly TIPS and TBS) combine with cyclic N-alkenyl N-acyliminium salts generated in situ from their N,O-acetal precursors, to furnish highly functionalized indolizidines through an unprecedented double Mukaiyama–Mannich–Prins cascade transformation. This novel cascade annulation process demonstrates a promising scope, and takes place mostly catalytically with interesting stereocontrol. Furthermore, an appealing facet of this chemistry is emphasized with a bicatalytic approach by which the Mannich–Prins cascade follows a Ru-catalyzed N-allylamide to N-(E)-propenyl isomerization of the aminal counterpart in a one-pot operation. © 2018 Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02413309
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Submitted on : Monday, December 16, 2019 - 10:45:07 AM
Last modification on : Friday, January 31, 2020 - 11:16:02 AM

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Mathéo Berthet, Alice Beauseigneur, Charlotte Moine, Catherine Taillier, Mohamed Othman, et al.. Novel Hybrid Prins/Aza-Prins Oxocarbenium/N-Acyliminium Cascade Expedient Access to Complex Indolizidines. Chemistry - A European Journal, Wiley-VCH Verlag, 2018, 24 (6), pp.1278-1282. ⟨10.1002/chem.201705949⟩. ⟨hal-02413309⟩

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