biostudies-literatureRomaniszyn MNarodowe Centrum Nauki7722-7726https://www.ebi.ac.uk/biostudies/studies/S-EPMC9623593biostudies-literatureUnknown24(42)A novel organocatalytic reaction cascade between 3-cyano-4-styrylcoumarins and 2-mercaptoacetophenones is described. It is based on stereocontrolled functionalization of cyanocoumarins proceeding in a sequence of <i>thia</i>-Michael/aldol/annulation reactions. This highly diastereo- and enantioselective reaction is realized by employing enantioselective bifunctional catalysis and exhibits a broad substrate scope and excellent functional group tolerance. The synthetic application involves the transformation of the imidoester group, thus opening access to biologically relevant coumarin and δ-lactone-fused products.Organic lettersOrganocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis.PMC9623593UMO-2015/18/E/ST5/00309Romaniszyn MDybowska JAlbrecht LSkrzynska AfalseOrganocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis.A novel organocatalytic reaction cascade between 3-cyano-4-styrylcoumarins and 2-mercaptoacetophenones is described. It is based on stereocontrolled functionalization of cyanocoumarins proceeding in a sequence of <i>thia</i>-Michael/aldol/annulation reactions. This highly diastereo- and enantioselective reaction is realized by employing enantioselective bifunctional catalysis and exhibits a broad substrate scope and excellent functional group tolerance. The synthetic application involves the transformation of the imidoester group, thus opening access to biologically relevant coumarin and δ-lactone-fused products.2022-01-01T00:00:00Z2022 Oct2025-04-18T22:50:54.272Z2025-04-07T10:32:55.131ZS-EPMC96235933625295510.1021/acs.orglett.2c02836