Abstract
Novel chiral P,N-bidentate arylphosphites have been prepared by a one-step phosphorylation of appropriate hydroxy ketimines based on (R )-(+)-camphor. Metal chelate complexes [Rh(CO)(PN)Cl] and [Pd(PN)(allyl)]BF4 with the ligands were obtained and the new compounds were fully characterized by 1 H, 13 C and 31 P NMR, IR, MS (EI, FAB and ESI techniques) and X-ray crystal structure analysis. Using these ligands, up to 73% ee has been achieved in the asymmetric palladium-catalyzed sulfonylation of 1,3-diphenyl-2-propenyl acetate with sodium p -toluenesulfinate. In the enantioselective alkylation of the same substrate with dimethyl malonate, up to 94% enantioselectivity has been achieved.
Key words
allylations - asymmetric catalysis - chiral ketimines - palladium - P,N-ligands
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