Carbene-Catalyzed Activation of Formyl-phenylacetic Esters for Access to Chiral Dihydroisoquinolinones

Abstract

A carbene-catalyzed reaction to synthesize chiral dihydroisoquinolinones via an <i>o</i>-quinodimethane (<i>o</i>-QDM) intermediate is disclosed. <i>o</i>-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.