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Stereoselective and Catalytic Access to β-Enaminones: An Entry to Pyrimidines

Eric Gayon, Monika Szymczyk, Hélène Gérard*, Emmanuel Vrancken* and Jean-Marc Campagne*

*Institut Charles Gerhardt UMR 5253 CNRS-UM2-UM1-ENSCM, 8 rue de l’Ecole Normale, 34296 Montpellier Cedex 5; France, UPMC-Université Paris 06, CNRS case 137, 4 Place Jussieu, 75262 Paris Cedex 05, France, Email:;;

E. Gayon, M. Szymczyk, H. Gérard, E. Vrancken, J.-M. Campagne, J. Org. Chem., 2012, 77, 9205-9220.

DOI: 10.1021/jo301675g (free Supporting Information)

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A NaOH catalyzed rearrangement of propargylic hydroxylamines allows a highly stereoselective access to Cbz-protected β-enaminones. A subsequent synthesis of pyrimidines shows the synthetic potential of these β-enaminones.

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Key Words

β-enaminones, pyrimidines

ID: J42-Y2012-3280