Palladium-catalysed asymmetric allylation and complex formation involving P,N-bidentate diamidophosphites with 1,3,2-diazaphospholidine cycles |
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Authors: | Konstantin N Gavrilov Sergey V Zheglov Alexei A Shiryaev |
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Institution: | a Department of Chemistry, Ryazan State Pedagogic University, 46 Svoboda Str., Ryazan 390000, Russia b Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Str., Moscow 119991, Russia |
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Abstract: | New chiral P,N-bidentate 1,3,2-diazaphospholidine ligands were obtained by one-step phosphorylation of (2S,3S)-2-(ferrocenylideneamino)-3-methylpentan-1-ol and (4S,5S)-(−)-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(η2-P,N)] and , 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 complexes as chiral catalysts. |
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Keywords: | Chiral P N-ligands Diamidophosphites Palladium Rhodium Asymmetric allylation |
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