Atropselective alkylation of biaryl compounds by means of transition metal-catalyzed C-H/olefin coupling

The reaction of 2-(1-naphthyl)-3-methylpyridine with olefins in the presence of [RhCl(coe)(2)](2) and PCy3 as the catalyst resulted in the alkylation of the naphthyl ring at the 2-position in good yield. The replacement of PCy3 with the chiral ferrocenyl phosphine, (R),(S)-PPFOMe, as the ligand resulted in atropselective alkylation of the naphthylpyridine derivatives. Ethylene reacted with the biaryl compounds to give the corresponding addition products in moderate yields with fair to good ee's (up to 49% ee). (C) 2000 Elsevier Science Ltd. All rights reserved.