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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

OH-Pd(0) interaction as a stabilizing factor in palladium-catalyzed allylic alkylations.

In palladium-catalyzed alkylations of allylic acetates with malonate as nucleophile, catalysts with oxazoline ligands bearing hydroxymethyl substituents in 4-position have been shown by density functional theory computations to undergo a conformational change on nucleophilic attack, which is accompanied by reduction of Pd(II) to Pd(0). The conformations of the Pd(0) complexes were shown to be governed by the presence of a hydrogen bond with the metal center acting as a hydrogen bond acceptor. The conformational change, which is absent in catalysts with O-alkylated analogs, largely affects the enantioselectivity of the catalytic process. This process is a previously uninvestigated example of where this type of weak hydrogen bond has been shown to influence the stereochemistry of a chemical reaction.[1]


  1. OH-Pd(0) interaction as a stabilizing factor in palladium-catalyzed allylic alkylations. Hallman, K., Frölander, A., Wondimagegn, T., Svensson, M., Moberg, C. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
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