Carbene-Catalyzed Activation of Formyl-phenylacetic Esters for Access to Chiral Dihydroisoquinolinones
Shuquan Wu, Jun Xu, Rui Deng, Hongling Wang, Yonggui Robin, Pengcheng Zheng
Abstract
A carbene-catalyzed reaction to synthesize chiral dihydroisoquinolinones via an o-quinodimethane (o-QDM) intermediate is disclosed. o-QDM reacts with cyclic sulfonic imines via annulation to afford highly enantioenriched dihydroisoquinolinone products. ESI-HRMS studies suggest a stepwise Mannich addition and acylation reaction pathway, and the pathways of the catalytic and uncatalyzed background reactions are evaluated via DFT calculations.
Topics & Concepts
ChemistryCarbeneCatalysisAnnulationAcylationCombinatorial chemistryMedicinal chemistryOrganic chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCyclopropane Reaction MechanismsSynthetic Organic Chemistry Methods