Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine-Transition-Metal Complexes. 6. Practical Asymmetric Synthesis of 1,1'-Binaphthyls via Asymmetric Cross-Coupling with a Chiral monophosphine/Nickel Catalyst.

Article abstract of DOI:10.1021/ja00232a030

Cross-coupling of (2-methyl-1-naphthyl)magnesium bromide (1a) with 2-methyl-1-naphthyl bromide (2a) at -15 or 0 deg C in the presence of nickel catalyst prepared in situ from nickel bromide and (S)-1-<(R)-2-(diphenylphosphino)ferrocenyl>ethyl methyl ether (3a) gave high yield of (R)-(-)-2,2'-dimethyl-1,1'-binaphthyl (4a) in up to 95percent ee.Ferrocenylphosphine 3a was also effective for the reaction of 1a with 1-naphthyl bromide (2b) and that of (2-ethyl-1-naphthyl)magnesium bromide (1c) with 2b to give corresponding cross-coupling products in 83 and 77percent ee, respectively.