Total synthesis N–H (+)-tetrahydro deoxycytisine and application in Pd-catalyzed hydroarylation of ketimine

We have recently reported the synthesis of NH-(+)-tetrahydro deoxycytisine from readily available piperidine. The synthesis mainly involved decarboxylative addition, chiral resolution, Dieckmann condensation, Mannich reaction and Wolff-Kishner reduction reactions. The chiral diamine was obtained in 7 steps with 3.1% overall yield. This chiral ligand has proved to be an efficient inducing agent for the Pd-catalyzed addition reaction of aryl boronic acid onto the cyclic sulfonyl imines in water.