title: A cooperative participation of the amido group in the organocatalytic construction of all-carbon quaternary stereocenters by Michael addition with β-ketoamides.
abstract: The secondary amido group of α-substituted β-ketoamides plays a crucial role in the control of the reactivity and spatial arrangement (selectivity) in the organocatalyzed Michael addition to unsaturated carbonyls. This results in an unprecedented activation mode of substrates through H-bonding interactions allowing the construction of enantiomerically enriched functionalized all-carbon quaternary centers and spiroaminals of high synthetic potential.
authors.affiliation: Aix-Marseille Université, iSm2, UMR CNRS 6263, Centre St Jérôme, service 531, 13397 Marseille Cedex 20, France.
authors.forename: Maria del Mar
authors.initials: Mdel M
authors.lastname: Sanchez Duque
authors.forename: Olivier
authors.initials: O
authors.lastname: Baslé
authors.forename: Nicolas
authors.initials: N
authors.lastname: Isambert
authors.forename: Anouk
authors.initials: A
authors.lastname: Gaudel-Siri
authors.forename: Yves
authors.initials: Y
authors.lastname: Génisson
authors.forename: Jean-Christophe
authors.initials: JC
authors.lastname: Plaquevent
authors.forename: Jean
authors.initials: J
authors.lastname: Rodriguez
authors.forename: Thierry
authors.initials: T
authors.lastname: Constantieux
mesh_terms: D000577:Amides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D013141:Spiro Compounds; C520957:beta-ketoamide; D002244:Carbon