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
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Publikationsverlauf

Publikationsdatum:
21. Dezember 2010 (online)

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.