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Modular Approach To New Chiral Monodentate Diamidophosphite Ligands. Application In Palladium-Catalyzed Asymmetric Hydrovinylation Of Styrene

I. Ayora, R.Ma. Ceder, M. Espinel, G. Muller, Mercè Rocamora, Marta Serrano
Published 2011 · Chemistry

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A new group of chiral monodentate diamidophosphite ligands (2 P−N/1 P−O bond) based on diazaphospholidine backbones derived from N,N′-dibenzylcyclohexane-1,2-diamine (7) and N,N′-dimethylcyclohexane-1,2-diamine (8), and diazaphosphepine backbones derived from N,N′-dimethyl-[1,1′-binaphthyl]-2,2′-diamine (9) and various chiral alkoxy groups (coming from phenylethanol a, borneol b, methyllactate c, allylic alcohol d, and methanol e) were prepared. The ligands have a highly modular structure, which is well suited to the synthesis of a small library. Preparation was readily accomplished by the successive addition of pure enantiomeric substituted diamine and pure enantiomeric alcohol to phosphorus trichloride. The corresponding diamidophosphite selenides Se(7−9) were prepared and the JPSe was calculated in order to evaluate the σ-donor ability of the new ligands. The reaction of [Pd(μ-Cl)(η3-2-CH3C3H4)]2 with the new diamidophosphite ligands (7−9) led to the monomeric allylic neutral complexes 11−13. Two isome...

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