Synfacts 2011(1): 0061-0061  
DOI: 10.1055/s-0030-1259108
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Rhodium-Catalyzed Addition of Arylboronic Acids to Alkenylheteroarenes

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
G. Pattison, G. Piraux, H. W. Lam*
University of Edinburgh, UK
Further Information

Publication History

Publication Date:
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.