engleski

Chiroptical properties and enantioselectivity in hydrogenation with rhodium(I) complexes of chiral bis-diphenylphosphines derived from D-glucose and D-galactose

(2R, 3S)-2-Diphenylphosphinomethyl-3-diphenylphosphinotetrahydropyran (3) has been prepared in 64% yield from the dimesylate 5, derived from D-galactose. The surprisingly different reactivities of dimesylates 2 and 5 towards diphenylphosphide anion are considered and the conformational properties of 1-6 discussed in terms of their CD spectra. The rhodium(I) complexes 9 and 10 exhibit low to relatively high enantioselectivities in hydrogenation of Z-α -acetylaminocinnamic acid and α -acetylaminoacrylic acid. The chiroptical and conformational properties of the bidentate ligands (3, 6), and their rhodium(I) complexes (9, 10) are correlated with the observed enantioselectivities.

Z-α -acetylaminocinnamic acid ; α -acetylaminoacrylic acid ; bidentate ligands (3 ; 6)

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