Integrated experimental and computational approach provides a rationale for the mode of action of cinchonabased alkaloids as chiral receptors in the observed dynamic chiral resolution of the titled tandem reaction. In particular, a mechanism based on a dynamic kinetic asymmetric transformation has been unravelled in detail. Furthermore, the crucial role of “distal” H-bonding donor functionality in directing the enantioselectivity reversal of homochiral cinchona-based catalysts has been convincingly explained. The access to enantiopure tertiary isoindolinone N,S-acetals has been achieved for the first time.

Desymmetrization of 2‐cyano‐N‐tosylbenzylidenimine with thiols and organocatalytic heterocyclization by dynamic resolution: mechanism investigation

Amalia Velardo;Vito Capaccio;Tonino Caruso;Antonia Di Mola;Antonio Massa;Consiglia Tedesco;Lucia Caporaso;Laura Falivene
;
Laura Palombi
2019

Abstract

Integrated experimental and computational approach provides a rationale for the mode of action of cinchonabased alkaloids as chiral receptors in the observed dynamic chiral resolution of the titled tandem reaction. In particular, a mechanism based on a dynamic kinetic asymmetric transformation has been unravelled in detail. Furthermore, the crucial role of “distal” H-bonding donor functionality in directing the enantioselectivity reversal of homochiral cinchona-based catalysts has been convincingly explained. The access to enantiopure tertiary isoindolinone N,S-acetals has been achieved for the first time.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/4730736
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