Polymer-supported phosphoramidites: Highly efficient and recyclable catalysts for asymmetric hydrogenation of dimethylitaconate and dehydroamino acids and esters

Simon Doherty, Edward G. Robins, Ibolya Pál, Colin R. Newman, Christopher Hardacre, David Rooney, Damian A. Mooney

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Several novel phosphoramidites have been prepared by reaction of the primary amines para-vinylaniline, ortho-anisidine, 2-methoxyphenyl(4-vinylbenzyl)amine, 8-aminoquinoline and 3-vinyl-8-aminoquinoline with (S)-1,1′-bi-2-naphthylchlorophosphite, in the presence of base. Rhodium(I) complexes of these phosphoramidites catalyse the asymmetric hydrogenation of dimethylitaconate and dehydroamino acids and esters giving ee values up to 95%. Soluble non-cross linked polymers of the para-vinylaniline and 3-vinyl-8-aminoquinoline-based phosphoramidites have been prepared by free radical co-polymerisation with styrene in the presence of AIBN as initiator. The corresponding [Rh(COD)]+ complexes serve as recyclable catalysts for the asymmetric hydrogenation dimethylitaconate and dehydroamino acids and esters to give ee values up to 80%.

    Original languageEnglish
    Pages (from-to)1517-1527
    Number of pages11
    JournalTetrahedron Asymmetry
    Volume14
    Issue number11
    DOIs
    Publication statusPublished - 6 Jun 2003

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