Asymmetric Ru/Cinchonine Dual Catalysis for the One-Pot Synthesis of Optically Active Phthalides from Benzoic Acids and Acrylates
Dattatraya H. Dethe, Nagabhushana C. Beeralingappa, Salman Siddiqui, Prakash N. Chavan
Abstract
Herein, we report the asymmetric Ru/cinchonine dual catalysis that provides straightforward access to enantioselective synthesis of C-3 substituted phthalides via tandem C–H activation/Michael addition cascade. The use of readily accessible and less expensive [RuCl2(p-cym)]2 and cinchonine catalyst for the one-pot assembly of chiral phthalides greatly overcomes the present trend of using highly sophisticated catalysts. The developed method provides access to both enantiomers of a product using pseudoenantiomeric cinchona alkaloids as catalysts streamlining the synthesis of phthalide in both the optically active forms.
Topics & Concepts
CinchonineChemistryPhthalideCinchonidineEnantioselective synthesisCatalysisCombinatorial chemistryOptically activeEnantiomerOrganic chemistryCinchona AlkaloidsEnantiomeric excessCinchonaCascade reactionBenzoic acidCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis