Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines
Luo Ge, Mercedes Zurro, Syuzanna R. Harutyunyan
Abstract
Chiral indole derivatives are ubiquitous motifs in pharmaceuticals and alkaloids. Herein, the first protocol for catalytic asymmetric conjugate addition of Grignard reagents to various sulfonyl indoles, offering a straightforward approach for the synthesis of chiral 3-sec-alkyl-substituted indoles in high yields and enantiomeric ratios is presented. This methodology makes use of a chiral catalyst based on copper phosphoramidite complexes and in situ formation of vinylogous imine intermediates.
Topics & Concepts
Indole testPhosphoramiditeImineChemistryCatalysisReagentIn situEnantiomerEnantioselective synthesisCombinatorial chemistryConjugateAlkylSulfonylCopperOrganic chemistryOligonucleotideBiochemistryDNAMathematicsMathematical analysisAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions