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

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Integrated experimental and computational approach provides a rationale for the mode of action of cinchona-based 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.
Original languageEnglish (US)
Pages (from-to)7584-7589
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number46
DOIs
StatePublished - Nov 28 2019

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