Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton
Amit Shikari, Koushik Mandal, Deepak Chopra, Subhas Chandra Pan
Abstract
Abstract An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ ‐hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo‐ and 86% to >99% enantioselectivities from a range of substituted isatins and γ ‐hydroxy enones. magnified image
Topics & Concepts
ChemistryIsatinSquaramideBifunctionalDominoOrganocatalysisCascade reactionCatalysisEnantioselective synthesisCombinatorial chemistryOrganic chemistryStereochemistryAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsSynthesis and Catalytic Reactions