Biomimetic asymmetric reduction of benzoxazinones and quinoxalinones using ureas as transfer catalysts
Zi‐Biao Zhao, Zi‐Biao Zhao, Xiang Li, Mu‐Wang Chen, Zongbao K. Zhao, Zongbao K. Zhao, Yong‐Gui Zhou
Abstract
Using ureas as transfer catalysts through hydrogen bonding activation, biomimetic asymmetric reduction of benzoxazinones and quinoxalinones with chiral and regenerable NAD(P)H models was described, giving chiral dihydrobenzoxazinones and dihydroquinoxalinones with high yields and excellent enantioselectivities. A key dihydroquinoxalinone intermediate of a BRD4 inhibitor was synthesized using biomimetic asymmetric reduction.
Topics & Concepts
CatalysisReduction (mathematics)ChemistryTransfer hydrogenationCombinatorial chemistrySelective catalytic reductionOrganic chemistryRutheniumGeometryMathematicsSynthesis and Biological EvaluationAsymmetric Synthesis and CatalysisChemical Synthesis and Analysis