Aminophosphine-oxazoline and phosphoramidite-oxazoline ligands and their application in asymmetric catalysis

摘要

The synthesis of a novel series of aminophosphine-oxazoline and phosphoramidite-oxazoline is described. The efficacy of these aminophosphine-oxazoline ligands was investigated in the palladium catalysed asymmetric allylic alkylation of 1,3-diphenylprop-2-enyl acetate leading to a maximum of 38% ee at 64% conversion. Phosphoramidite-oxazoline ligands, however, gave ees of up to 87% at 71% conversion in the same reaction and also proved to be effective in the palladium catalysed asymmetric Suzuki coupling between 2-methylnaphthylboronic acid and 1-bromonaphthalene, leading to a maximum of 46% ee in 54% isolated yield at room temperature. (C) 2007 Published by Elsevier Ltd.