Abstract
New chiral P,N-bidentate 1,3,2-diazaphospholidine ligands were obtained by one-step phosphorylation of (2 S,3 S)-2-(ferrocenylideneamino)-3-methylpentan-1-ol and (4 S,5 S)-(−)-2-methyl-4-hydroxymethyl-5-phenyl-2-oxazoline. Complexation of the new ligands with [Rh(CO) 2Cl] 2 and [Pd(allyl)Cl] 2 was found to give chelate complexes [Rh(CO)Cl(η 2-P,N)] and [ Pd ( allyl ) ( η 2 - P , N ) ] + BF 4 - , correspondingly. With the new P,N-ligands, up to 70% ee was achieved in the asymmetric Pd-catalysed sulfonylation of 1,3-diphenyl-2-propenyl acetate with sodium p-toluenesulfinate. In the enantioselective alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate, up to 91% enantioselectivity was achieved by using [ Pd ( allyl ) ( η 2 - P , N ) ] + BF 4 - complexes as chiral catalysts.
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