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. 2003 Mar 21:(6):732-3.
doi: 10.1039/b300033h.

Kumada-Corriu coupling of Grignard reagents, probed with a chiral Grignard reagent

Bettina Hölzer  1 , Reinhard W Hoffmann
Affiliations

Kumada-Corriu coupling of Grignard reagents, probed with a chiral Grignard reagent

Bettina Hölzer et al. Chem Commun (Camb). .

Abstract

The Grignard reagent 2, in which the magnesium-bearing carbon atom is the sole stereogenic centre has been coupled with vinyl bromide under Pd(0) or Ni(0)-catalysis to give compound 3 with full retention of configuration. Coupling using Fe(acac)3 or Co(acac)2 as catalyst was accompanied by considerable racemisation. These findings are discussed with respect to a dichotomy between concerted polar and stepwise SET transmetallation pathways.

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