Journal of Organic Chemistry p. 5074 - 5077 (1981)
Update date:2022-07-29
Topics:
Walborsky, H. M.
Banks, R. Bruce
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.
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