Abstract
Abstract A new MOP ligand ( 1b ), ( R )-(+)-2-(bis(3-trifluoromethylphenyl)phosphino)-2′-methoxy-1,1′-binaphthyl, was found to be more enantioselective than other MOP ligands for the palladium-catalyzed asymmetric reduction of α,α-disubstituted allylic esters with formic acid. The reduction of dl -2-(1-naphthyl)-3-buten-2-yl benzoate gave 3-(1-naphthyl)-1-butene of 90% ee. The higher enantioselectivity of 1b is ascribed to fast syn – anti isomerization of π-allylpalladium intermediates formed by oxidative addition of allylic ester to a palladium(0) species. The rate of syn – anti isomerization was measured by the magnetization saturation transfer in 1 H NMR.
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