N -benzyloxyacrylamides as bisnucleophiles in an organocatalyzed domino aza-Michael/Morita-Baylis-Hillman sequence - Unité de Recherche en Chimie Organique et Macromoléculaire Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2024

N -benzyloxyacrylamides as bisnucleophiles in an organocatalyzed domino aza-Michael/Morita-Baylis-Hillman sequence

Résumé

We herein describe a stereoselective organocatalyzed aza-Michael/Morita-Baylis-Hillman domino reaction between readily accessible acrylamides and α,β-unsaturated carbonyls. This novel, PPh$_3$-promoted atom economic one-pot process features medium to good yields and good stereoselectivity leading to variously substituted piperidin-2-ones bearing an exocyclic olefinic bond, which was shown to be an excellent anchor for further chemical diversification.

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Chimie
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Dates et versions

hal-04481372 , version 1 (28-02-2024)

Identifiants

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Ismail Alahyen, Catherine Taillier, Jérôme Lhoste, Vincent Dalla, Sébastien Comesse. N -benzyloxyacrylamides as bisnucleophiles in an organocatalyzed domino aza-Michael/Morita-Baylis-Hillman sequence. Organic Letters, In press, ⟨10.1021/acs.orglett.4c00295⟩. ⟨hal-04481372⟩
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