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Asymmetric Rhodium-Catalyzed Addition of Arylboronic Acids to Alkenylheteroarenes
G. Pattison, G. Piraux, H. W. Lam*
University of Edinburgh, UK
21 December 2010 (online)
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.