Stereochemistry of Transition-Metal-Catalyzed Cross-Coupling Reactions

Article abstract of DOI:10.1021/jo00338a004

The stereochemical results of transition-metal-catalyzed cross-coupling of methyllithium with chiral (+)-(S)-(4-methylcyclohexylidene)bromomethane (1) are reported.The use of bis(triphenylphosphine) dichlorocobalt(II), iron(III) tris(dibenzoylmethide), and dichloro<1,2-bis(diphenylphosphino)ethane>nickel(II) yielded chiral 1-methyl-4-ethylidenecyclohexane (2) with 89percent, 96percent, and 96percent retention of configuration, respectively.By contrast, the use of silver bromide yielded totally racemic product.