Desymmetrization of 2-Cyano-N-tosylbenzylidenimine with Thiols and Organocatalytic Heterocyclization by Dynamic Resolution: Mechanism Investigation
Di Mola, Antonia
KAUST DepartmentKAUST Catalysis Center (KCC)
Online Publication Date2019-11-28
Print Publication Date2019-12-15
Embargo End Date2020-11-06
Permanent link to this recordhttp://hdl.handle.net/10754/660563
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AbstractIntegrated 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.
CitationVelardo, A., Capaccio, V., Caruso, T., Di Mola, A., Massa, A., Tedesco, C., … Palombi, L. (2019). Desymmetrization of 2-Cyano-N -tosylbenzylidenimine with Thiols and Organocatalytic Heterocyclization by Dynamic Resolution: Mechanism Investigation. European Journal of Organic Chemistry, 2019(46), 7584–7589. doi:10.1002/ejoc.201901499
SponsorsWe thank Miur and University of Salerno for financial supports.