engleski

Preparation of chiral diphenylphosphines from D-glucose and enantioselective hydrogenation with their Rh(I) complexes

(2R, 3S)-2-Methylsulfonyloxymethyl-3-methylsulfonyloxy-tetrahydropyran (4), derived from D-glucose, is diphenylphosphinated to (2R, 3R)-2-diphenylphosphinomethyl-3-diphenylphosphino-tetrahydropyran (7), which is formed as a minor product. Compound 8 is the predominant product formed on 3, 4-elimination. Preparation and characterization of the rhodium(I) complexes 10-12 is described. Complex 10 of bidentate ligand 7 exhibits in hydrogenation of Z-alpha-N-acetylaminocinnamic acid enentioselectivity comparable to that obtained with rhodium(I) complex of (-)-DIOP (~70% e.e.). Saturated monoposphine, (2S)-2-diphenylphosphinomethyl-tetrahydropyran (9) affords mixed rhodium(I) complex (11, 12), which exhibits low enentioselectivity.

rhodium(I) complexes ; hydrogenation of Z-alpha-N-acetylaminocinnamic acid

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