Bulletin of the Chemical Society of Japan · 2001 · 44 citations · 60 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalyst DesignCatalyst SynthesisCatalytic MaterialsHeterocyclic ChemistryHeterogeneous CatalysisSupported CatalystsAldehydesCatalyst Structure - Activity RelationshipsCatalytic Reaction MechanismsChiral Catalyst DesignEnantioselective Catalyst DesignHetero Diels - Alder ReactionHeterocyclic CatalystsMolecular Catalysts
Abstract Optically active 3-oxobutylideneaminatocobalt(III) complexes were developed as effective catalysts for the enantioselective hetero Diels–Alder reaction of aromatic and aliphatic aldehydes with 3-(t-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene. In the presence of the highly active cationic cobalt(III) complex, the hetero Diels–Alder reactions proceeded to afford the corresponding dihydropyran-4-ones with high performance and high enantioselectivities. The reaction with aromatic aldehydes substituted by a coordinating group at the ortho position proceeded more smoothly.
60