Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds
Hui-Chun Wu, Chen Wang, Ying-Han Chen, Yankai Liu
Abstract
An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary stereocenter with excellent stereoselectivities.
Topics & Concepts
NonaneNucleophileMichael reactionChemistryCascadeOrganocatalysisStereochemistryOrganic chemistryCatalysisEnantioselective synthesisChromatographyAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsChemical synthesis and alkaloids