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

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  2. Dr Simon Doherty
  3. Dr Edward Robins
Author(s)Doherty S; Robins EG; Pal I; Newman CR; Hardacre C; Rooney D; Mooney DA
Publication type Article
JournalTetrahedron: Asymmetry
Year2003
Volume14
Issue11
Pages1517-1527
ISSN (print)0957-4166
ISSN (electronic)1362-511X
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Several novel phosphoramidites have been prepd. 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 catalyze the asym. hydrogenation of dimethylitaconate and dehydroamino acids and esters giving ee values up to 95%. Sol. noncrosslinked polymers of the para-vinylaniline and 3-vinyl-8-aminoquinoline-based phosphoramidites have been prepd. by free radical co-polymn. with styrene in the presence of AIBN as initiator. The corresponding [Rh(COD)]+ complexes serve as recyclable catalysts for the asym. hydrogenation dimethylitaconate and dehydroamino acids and esters to give ee values up to 80%.
PublisherPergamon
URLhttp://dx.doi.org/10.1016/S0957-4166(03)00253-2
DOI10.1016/S0957-4166(03)00253-2
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