Enantioselective Palladium-Catalyzed Arylborylation/Cyclization of Alkenes to Access Boryl-Functionalized Heterocyclic Compounds Containing Quaternary Stereogenic Centers.

Asymmetric palladium-catalyzed arylboration/cyclization of both nonactivated and activated alkenes with B 2 pin 2 was developed. A wide range of N -allyl- o -iodobenzamides and o -iodoacryanilides reacted with B 2 pin 2 to afford borylated 3,4-dihydroisoquinolinones and oxindoles, respectively, in high yields with high enantioselectivities. The synthetic utility of this enantioselective protocol was highlighted by synthesizing various chiral 3,4-dihydroisoquinolinone and oxindole derivatives containing quaternary stereogenic carbon centers, including enantioenriched Roche anticancer agent ( S )-RO4999200.