Schnitzler, V., Nonglaton, G., Roussiere, H., Maillet, C., Evain, M., Janvier, P., Bujoli, B. & Petit, M. (2008) Nitrogen-Based Chirality Effects in Novel Mixed Phosphorus/Nitrogen Ligands Applied to Palladium-Catalyzed Allylic Substitutions. Organometallics, 27 5997–6004.
Added by: Laurent Cournède (2016-03-10 21:58:40)
|Type de référence: Article
Numéro d'identification (ISBN etc.): 0276-7333
Clé BibTeX: Schnitzler2008
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Mots-clés: acid-derivatives, alkylation, amination, asymmetric catalysis, complexes, enantioselective catalysis, hydrogenation, phosphinoaryloxazolines, semicorrins, thioglucose
Créateurs: Bujoli, Evain, Janvier, Maillet, Nonglaton, Petit, Roussiere, Schnitzler
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A novel series of chiral P,N-ligands was obtained by desymmetrization of the achiral meso-N,N'-dimethyl-1,2-diphenylethane-1,2-diamine backbone and resolution of the resulting adducts. This transformation was achieved by the selective introduction of a diphenylphosphine moiety on one of the two nitrogen centers. The resulting palladium complexes were used for the catalytic enantioselective allylic alkylation of 1,3-diphenyl-1-acetoxy-2-propene with dimethyl malonate. In some cases, high conversions (up to 98\% after 1 h) along with good chiral inductions (up to 95\% e.e.) were obtained, as a result of a control of the inversion of the stereogenic center formed at nitrogen upon coordination to palladium.
Added by: Laurent Cournède