Publication:
Polymer-supported phosphoramidites: highly efficient and recyclable catalysts for asymmetric hydrogenation of dimethylitaconate and dehydroamino acids and esters 2003
Doherty, Simon; Robins, Edward G.; Pal, Ibolya; Newman, Colin R.; Hardacre, Christopher; Rooney, David; Mooney, Damian A
Abstract
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%.
- Tetrahedron: Asymmetry
- Volume: 14
- Number: 11
- Pagination: 1517-1527
- Date: 2003-05-20
- ISBN/ISSN: 1362-511X
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Dr Simon Doherty
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