Asymmetric Rhodium-Catalyzed Addition of Arylboronic Acids to Alkenylheteroarenes

Significance

In this paper the authors report the first catalytic enantioselective addition of arylboronic acids and alkenyl N-methyliminodiacetic acid (MIDA) boronate to β-substituted alkenyl­heteroarenes. Various types of substrates were employed, containing π-deficient quinoline, quin­oxaline, pyrimidine moieties as well as π-excessive oxazole and oxadiazole fragments; the products were obtained in 56-91% yields and with 89-98% ee. Introduction of the alkenyl moiety could be ­accomplished via alkenyl MIDA boronates. Microwave irradiation could be replaced by thermal heating.