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Synfacts 2008(4): 0373-0373  
DOI: 10.1055/s-2008-1042874
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Asymmetric Hydrogenation of Itaconic Acid Mono-Esters

Contributor(s): Hisashi Yamamoto, Joshua P. Abell
K. F. W. Hekking, L. Lefort, A. H. M. de Vries, F. L. van Delft, H. E. Schoemaker, J. G. de Vries*, F. P. J. T. Rutjes*
Radbound University Nijmegen and DSM Pharmaceutical Products, Advanced Synthesis, Catalysis & Development, Geleen, The Netherlands
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Publikationsverlauf

Publikationsdatum:
19. März 2008 (online)

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Significance

The authors demonstrated optimized conditions to convert various itaconic acid mono-esters into the corresponding succinic acid derivatives with excellent conversion and high enantioselectivities. Using a library of mondentate phophoramidite/phosphate ligands, a large number of reaction conditions were screened using autoclave hydrogenation techniques. Using the optimized reaction conditions the authors demonstrated the asymmetric hydrogenation of their substrates on 1 g scale.