A Cooperative Participation of the Amido Group in the Organocatalytic Construction of All-Carbon Quaternary Stereocenters by Michael Addition with β-Ketoamides
Organic Letters2011Vol. 13(13), pp. 3296–3299
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Maria del Mar Sanchez Duque, Olivier Baslé, Nicolás Isambert, Anouk Gaudel‐Siri, Yves Génisson, Jean‐Christophe Plaquevent, Jean Rodriguez, Thierry Constantieux
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.
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