Asymmetric Synthesis of Cyclohexenone-Fused Isochromans via Quinidine-Catalyzed Domino Peroxyhemiacetalization/Oxa-Michael Addition/Desymmetrization Sequence
Tamanna, Yaseen Hussain, Deepak Sharma, Pankaj Chauhan
Abstract
A highly enantio- and diastereoselective synthesis of highly functionalized isochromans was achieved through an organocatalyzed domino reaction. Quinidine as the catalyst initiates a peroxyhemiacetalization/oxa-Michael/desymmetrization domino sequence between various 2,5-cyclohexadienone-tethered aryl aldehydes with hydroperoxides to generate the single diastereomers of isochromans appended with a cyclohexenone ring bearing three vicinal stereocenters in good yields and high enantioselectivities under ambient reaction conditions.
Topics & Concepts
DesymmetrizationChemistryStereocenterDominoDiastereomerCyclohexenoneMichael reactionStereochemistryOrganocatalysisCascade reactionCatalysisEnantioselective synthesisOrganic chemistryAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsMicrobial Natural Products and Biosynthesis