Catalytic Asymmetric 1,4-Reduction of α-Branched 2-Vinyl-azaarenes by a Chiral SPINOL-Derived Borophosphate
Yang Cao, Shouqi Zhang, Jon C. Antilla
Abstract
The catalytic asymmetric 1,4-reduction of α-branched 2-vinylazaarenes by a SPINOL-derived borophosphate has been realized. A SPINOL-derived phosphoric acid is used to form a bifunctional phosphoryl boronate catalyst in situ in the presence of pinacolborane. This asymmetric 1,4-reduction reaction provides a convenient procedure to access chiral alkylated quinolines and benzothiazoles in high yields (up to 94%) and with good stereoselectivities (up to 98%).
Topics & Concepts
BifunctionalCatalysisChemistryPhosphoric acidAlkylationCombinatorial chemistryReduction (mathematics)Bifunctional catalystEnantioselective synthesisOrganic chemistryMathematicsGeometryAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions