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Synfacts 2006(8): 0852-0852  
DOI: 10.1055/s-2006-941996
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

PEG-Supported Monodentate Phosphite Ligands

Contributor(s): Yasuhiro Uozumi, Takayasu Arakawa
W. Chen*, S. M. Roberts, J. Whittall*
University of Liverpool, UK
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

A new PEG-supported monophosphite ligand for asymmetric hydrogenation of itaconates, enamides, α-dehydroamino acid derivatives and β-dehydroamino acid derivatives has been developed. The asymmetric hydrogenation of dimethyl itaconate was carried out in the presence of a PEG-supported Rh catalyst which was generated in situ from Rh(cod)2OTf and ligand 1 to give dimethyl (S)-2-methylsuccinate in quantitative yield (97.4% ee) with TOF of >20000 h-1. This supported catalyst was applied to the asymmetric hydrogenation of a wide range of substrates (five examples).