84094-48-4Relevant academic research and scientific papers
Asymmetric Hydrogenation Using Diphenylphosphinite Derivatives of Carbohydrates as the Chiral Ligand of Rhodium Catalysts
Yamashita, Mitsuji,Naoi, Manabu,Imoto, Hiroyuki,Oshikawa, Tatsuo
, p. 942 - 944 (2007/10/02)
Diphenylphosphinite derivatives of carbohydrates (L-rhamnose, D-mannitol, and cellulose), which have asymmetric centers on the skeletons were synthesized.Asymmetric hydrogenations of prochiral substrates using rhodium catalysts with the prepared chiral phosphinite ligand were carried out to obtain chiral substances in 8-78percent optical yield.
Asymmetric Grignard Cross-Coupling Reaction Using Chiral Ligands Derived from Carbohydrates
Iida, Akihito,Yamashita, Mitsuji
, p. 2365 - 2368 (2007/10/02)
Chiral diphenylphosphine and diphenylphosphinite dervatives of carbohydrates such as D-glucose, D-galactose, and L-rhamnose were used as the ligand of metal catalysts for asymmetric Grignard cross-coupling reaction.Coupling of s-butylmagnesium bromide wit
Synthesis of Sugar Derivatives of Tervalent Phosphorus Compounds and Their Application to Homogeneous Asymmetric Hydrogenation
Yamashita, Mitsuji,Hiramatsu, Koji,Yamada, Manabu,Suzuki, Nobuyoshi,Inokawa, Saburo
, p. 2917 - 2921 (2007/10/02)
Diphenylphosphine and diphenylphosphinite derivatives of sugars such as methyl 6-deoxy-4-C-(diphenylphosphino)-2,3-O-isopropylidene-α-L-talopyranoside, methyl 4-O-(diphenylphosphino)-2,3-O-isopropylidene-α-L-rhamnopyranoside, methyl 4-C,4-O-(diphenylphosphino)-2,3-O-isopropylidene-α-L-talopyranoside, 6-deoxy-6-C-(diphenylphosphino)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose, and 6-O-(diphenylphosphino)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose were synthesized by the reaction of diphenylphosphine-sodium dihydrobis(2-methoxyethoxy)aluminate (SDMA) and/or diphenylphosphinous chloride-triethylamine with sugar derivatives.Homogeneous asymmetric hydrogenations of several prochiral olefins (α-acetylaminocinnamic acid, methyl α-acetylaminocinnamate, α-benzoylaminocinnamic acid, itaconic acid, and tiglic acid) were carried out using rhodium(I) catalysts with the tervalent chiral phosphorus derivatives of sugars.The highest optical yield for all the five substrates was obtained when di-μ-chloro-bis(cyclooctadiene)dirhodium(I) and 6-O-(diphenylphosphino)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose were used.The advantages of this method are the simplicity in the synthesis of the chiral phosphorus compound and the comparatively high optical yield in the asymmetric hydrogenation of olefins.
