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Efficient and Direct Synthesis of γ‐Amino‐α,β‐Unsaturated Amides by Catalyzed Allylic Substitution of α‐Fluoroenamides: Toward to Synthesis of Hybrid Peptides and Indolizidines

Abstract : A variety of γ‐amino‐α,β‐unsaturated amides have been synthesized from readily available α‐fluoroenamides precursors via an unprecedented intermolecular and intramolecular conjugative catalytic amination process. These γ‐amino‐α,β‐unsaturated amides are useful intermediates for accessing rarely synthesized hybrid peptides, αγα sequences, and various classes of alkaloids containing a pyrrolidine ring, as illustrated by total synthesis of the indolizidine alkaloid coniceine.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024526
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 19, 2019 - 11:10:51 AM
Last modification on : Thursday, July 2, 2020 - 3:28:42 AM

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K. Harsha Vardhan Reddy, Matthieu Bédier, Samir Bouzbouz. Efficient and Direct Synthesis of γ‐Amino‐α,β‐Unsaturated Amides by Catalyzed Allylic Substitution of α‐Fluoroenamides: Toward to Synthesis of Hybrid Peptides and Indolizidines. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2018, 2018 (12), pp.1455-1459. ⟨10.1002/ejoc.201800110⟩. ⟨hal-02024526⟩

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