Stereodivergent Construction of 1,3‐Chiral Centers via Tandem Asymmetric Conjugate Addition and Allylic Substitution Reaction
Jiahao Xie, Yi‐Ming Hou, Zuolijun Feng, Shu‐Li You
Abstract
Herein, we report a synthesis of cyclohexanones bearing multi-continuous stereocenters by combining copper-catalyzed asymmetric conjugate addition of dialkylzinc reagents to cyclic enones with iridium-catalyzed asymmetric allylic substitution reaction. Good to excellent yields, diastereoselectivity and enantioselectivity can be obtained. Unlike the stereodivergent construction of adjacent stereocenters (1,2-position) reported in the literature, the current reaction can achieve the stereodivergent construction of nonadjacent stereocenters (1,3-position) by a proper combination of two chiral catalysts with different enantiomers.
Topics & Concepts
StereocenterConjugateAllylic rearrangementSubstitution (logic)Enantioselective synthesisReagentEnantiomerTandemCombinatorial chemistryCatalysisStereochemistryChemistryComputer scienceMathematicsOrganic chemistryMaterials scienceProgramming languageMathematical analysisComposite materialAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods