Chiral bidentate ligands from the most widespread monosaccharides for enantioselective hydrogenation: diphenylphosphinites from d-glucose and d-xylose

(2 R, 3 S)-2-Diphenylphosphinoxymethyl-3-diphenylphosphinoxytetra-hydropyran (2) and (3 R, 4 R)-3,4-bis-diphenylphosphinoxytetrahydropyran (4) were prepared from D-glucose and D-xylose, respectively, and characterized as their Cu(I) complex salts (5 and 6). Rh(I) NBD (NBD = norborna-diene) complexes...

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Bibliographic Details
Published in:Journal of molecular catalysis 1987-10, Vol.42 (2), p.173-181
Main Authors: Habuš, Ivan, Raza, Zlata, Šunjić, Vitomir
Format: Article
Language:English
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Summary:(2 R, 3 S)-2-Diphenylphosphinoxymethyl-3-diphenylphosphinoxytetra-hydropyran (2) and (3 R, 4 R)-3,4-bis-diphenylphosphinoxytetrahydropyran (4) were prepared from D-glucose and D-xylose, respectively, and characterized as their Cu(I) complex salts (5 and 6). Rh(I) NBD (NBD = norborna-diene) complexes of 2 and 4 were used for the enantioselective hydrogenation of Z-α-acetylaminocinnamic acid. The complex of 2 afforded R-, while the complex of 4 afforded S-α-acetylaminophenylalanine, the enantiomeric excess (e.e.) being dependent on temperature. The highest e.e. (90.4%) was obtained with the Rh(I) complex of 4 at −15 °C.
ISSN:0304-5102
DOI:10.1016/0304-5102(87)85023-X