TY - JOUR
T1 - Desymmetrization of 2-Cyano-N-tosylbenzylidenimine with Thiols and Organocatalytic Heterocyclization by Dynamic Resolution: Mechanism Investigation
AU - Velardo, Amalia
AU - Capaccio, Vito
AU - Caruso, Tonino
AU - Di Mola, Antonia
AU - Massa, Antonio
AU - Tedesco, Consiglia
AU - Caporaso, Lucia
AU - Falivene, Laura
AU - Palombi, Laura
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We thank Miur and University of Salerno for financial supports.
PY - 2019/11/28
Y1 - 2019/11/28
N2 - 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.
AB - 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.
UR - http://hdl.handle.net/10754/660563
UR - http://doi.wiley.com/10.1002/ejoc.201901499
UR - http://www.scopus.com/inward/record.url?scp=85075952333&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201901499
DO - 10.1002/ejoc.201901499
M3 - Article
VL - 2019
SP - 7584
EP - 7589
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 46
ER -