The polymerizable rhodium complex [(+)-diopRh(AAEMA)] (AAEMA(-): deprotonated form of the ligand 2-(acetoacetoxy)-ethylmethacrylate) was obtained by reaction of (cod)Rh(AAEMA) with (+)-diop at -80 degreesC. Supported chiral complexes have been obtained by copolymerization of [(+)-diopRh(AAEMA)l with NN-dimethylacrylamide and N,N'-methylene-bisacrylamide or by reaction of [(+)-diopRhCl](2) with an opportunely prepared: poly(beta-ketoesterate). Catalytic tests carried out with the homogeneous catalyst or with both its heterogeneous analogues:proved to be active in the enantioselective hydrogenation of methyl-(Z)-alpha-N-acetamidocinnamate yielding (S)-phenylalanine methylester with ee's up to 67%. (C) 2002 Elsevier Science B.V. All rights reserved.
Synthesis and catalytic activity of new supported rhodium(I) complexes for the enantioselective hydrogenation of methyl-(Z)-alpha-N-acetamidocinnamate
GOBETTO, Roberto;
2002-01-01
Abstract
The polymerizable rhodium complex [(+)-diopRh(AAEMA)] (AAEMA(-): deprotonated form of the ligand 2-(acetoacetoxy)-ethylmethacrylate) was obtained by reaction of (cod)Rh(AAEMA) with (+)-diop at -80 degreesC. Supported chiral complexes have been obtained by copolymerization of [(+)-diopRh(AAEMA)l with NN-dimethylacrylamide and N,N'-methylene-bisacrylamide or by reaction of [(+)-diopRhCl](2) with an opportunely prepared: poly(beta-ketoesterate). Catalytic tests carried out with the homogeneous catalyst or with both its heterogeneous analogues:proved to be active in the enantioselective hydrogenation of methyl-(Z)-alpha-N-acetamidocinnamate yielding (S)-phenylalanine methylester with ee's up to 67%. (C) 2002 Elsevier Science B.V. All rights reserved.
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