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Kinetic resolution of racemic 2,2 -bis(trifluoromethanesulfonyloxy)-1,1 -binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst
Kinetic resolution of the racemic title compound was shown to take place during its methylation with either (Me 2 AlOCH 2 CH 2 OMe) 2 or Me 2 Al(CH 2 ) 3 NMe 2 in the presence of an optically active Pd(binap) catalyst, as well as during its alkylation with either (S)-(+)-[Me 2 AlOCH 2 CH(Me)OCH 2 Ph] 2 or (S)-(+)-[Me 2 AlOCH 2 CH(CH 2 CHMe 2 )NMe 2 ] 2 in the presence of an achiral palladium complex. The ee values of the resolved binaphthyl derivatives by the two methods were up to 69 and 12%, respectively. The latter method represents the first application of a stabilized dialkylaluminum complex with a chiral chelating ligand for asymmetric induction.