Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/<i>oxa</i>-Michael Addition between Propargylamines with Water
Xinwei He, Mengqing Xie, Ruxue Li, Pui Ying Choy, Qiang Tang, Yongjia Shang, Fuk Yee Kwong
Abstract
A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne–allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.
Topics & Concepts
ConjugateChemistryMichael reactionCascadeCombinatorial chemistryAddition reactionStereochemistryOrganic chemistryCatalysisChromatographyMathematical analysisMathematicsSynthesis of Indole DerivativesCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis