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

Asymmetric palladium-catalyzed arylboration/cyclization of both nonactivated and activated alkenes with B2pin2 was developed. A wide range of N-allyl-o-iodobenzamides and o-iodoacryanilides reacted with B2pin2 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.

Automated summary

Asymmetric palladium-catalyzed arylboration/cyclization of both nonactivated and activated alkenes with B2pin2 was developed to synthesize borylated 3,4-dihydroisoquinolinones and oxindoles with high yields and high enantioselectivities. The synthetic utility of this enantioselective protocol was demonstrated by synthesizing various chiral derivatives containing quaternary stereogenic carbon centers, including the enantioenriched Roche anticancer agent (S)-RO4999200.