| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1351397 | Tetrahedron: Asymmetry | 2011 | 9 Pages |
A series of monophosphite ligands derived from d-fructose and d-glucose have been synthesized and employed in Rh-catalyzed asymmetric hydrogenation of α- and β-dehydroamino acid esters. A variety of chiral α- and β-amino acid esters have been obtained in excellent enantiomeric excess (up to 98.4% ee).
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1,2:4,5-Di-O-isopropylidene-3-O-((R)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-d-fructoseC32H32O8PEe ⩾99%[α]D25=−430.5 (c 1.06, THF)Source of chirality:d-fructose and BINOLAbsolute configuration:(2S,3S,4R,5R,Ra)
1,2:4,5-Di-O-isopropylidene-3-O-((S)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-d-fructoseC32H32O8PEe ⩾99%[α]D25=+197.0 (c 1.20, THF)Source of chirality:d-fructose and BINOLAbsolute configuration:(2S,3S,4R,5R,Sa)
1,2:4,5-Di-O-cyclohexylidene-3-O-((R)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-d-fructoseC38H40O8PEe ⩾99%[α]D25=−382.45 (c 1.08, THF)Source of chirality:d-fructose and BINOLAbsolute configuration:(2S,3S,4R,5R,Ra)
1,2:4,5-Di-O-cyclohexylidene-3-O-((S)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-d-fructoseC38H40O8PEe ⩾99%[α]D25=+147.9 (c 0.98, THF)Source of chirality:d-fructose and stereoselective synthesisAbsolute configuration:(2S,3S,4R,5R,Sa)
1,2:4,5-Di-O-isopropylidene-3-O-((R)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-β-d-fructopyranoseC32H32O8PEe ⩾99%[α]D25=−360.7 (c 1.20, THF)Source ofchirality:d-fructose and BINOLAbsolute configuration:(2S,3R,4R,5R,Ra)
1,2:4,5-Di-O-isopropylidene-3-O-((S)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-β-d-fructopyranoseC32H32O8PEe ⩾99%[α]D25=+201.1 (c 0.89, THF)Source of chirality:d-fructose and BINOLAbsolute configuration:(2S,3R,4R,5R,Sa)
1,2:4,5-Di-O-cyclohexylidene-3-O-((R)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-β-d-fructopyranoseC38H40O8PEe ⩾99%[α]D25=−325.4 (c 1.05, THF)Source of chirality:d-fructose and stereoselective synthesisAbsolute configuration:(2S,3R,4R,5R,Ra)
1,2:4,5-Di-O-cyclohexylidene-3-O-((S)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-β-d-fructopyranoseC38H40O8PEe ⩾99%[α]D25=+151.8 (c 1.23, THF)Source of chirality:d-fructose and BINOLAbsolute configuration:(2S,3R,4R,5R,Sa)
1,2:4,5-Di-O-isopropylidene-3-O-(2,2′-O,O-(1,1′-biphenyl)dioxophosphite)-β-d-fructopyranoseC24H28O8PEe ⩾99%[α]D25=−123.6 (c 1.06, THF)Source of chirality:d-fructoseAbsolute configuration:(2S,3S,4R,5R)
1,2:5,6-Di-O-isopropylidene-3-O-((R)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-d-glucoseC32H32O8PEe ⩾99%[α]D25=−303.1 (c 1.14, THF)Source of chirality:d-glucose and BINOLAbsolute configuration:(1R,2R,3S,4R,5R,Ra)
1,2:5,6-Di-O-isopropylidene-3-O-((S)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-d-glucoseC32H32O8PEe ⩾99%[α]D25=+291.9 (c 1.11, THF)Source of chirality:d-glucose and BINOLAbsolute configuration:(1R,2R,3S,4R,5R,Sa)
1,2:5,6-Di-O-cyclohexylidene-3-O-((R)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-d-glucoseC38H40O8PEe ⩾99%[α]D25=−267.7 (c 1.13, THF)Source of chirality:d-glucose and BINOLAbsolute configuration:(1R,2R,3S,4R,5R,Ra)
1,2:5,6-Di-O-cyclohexylidene-3-O-((S)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-d-glucoseC38H40O8PEe ⩾99%[α]D25=+262.7 (c 1.08, THF)Source of chirality:d-glucose and BINOLAbsolute configuration:(1R,2R,3S,4R,5R,Sa)
1,2:5,6-Di-O-isopropylidene-3-O-((R)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-β-d-glucofuranoseC32H32O8PEe ⩾99%[α]D25=−248.7 (c 0.98, THF)Source of chirality:d-glucose and BINOLAbsolute configuration:(1R,2R,3R,4R,5R,Ra)
1,2:5,6-Di-O-isopropylidene-3-O-((S)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-β-d-glucofuranoseC32H32O8PEe ⩾99%[α]D25=+318.4 (c 1.15, THF)Source of chirality:d-glucose and BINOLAbsolute configuration:(1R,2R,3R,4R,5R,Sa)
1,2:5,6-Di-O-cyclohexylidene-3-O-((R)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-β-d-glucofuranoseC38H40O8PEe ⩾99%[α]D25=−192.45 (c 1.00, THF)Source of chirality:d-glucose and BINOLAbsolute configuration: (1R,2R,3R,4R,5R,Ra)
1,2:5,6-Di-O-cyclohexylidene-3-O-((S)-2,2′-O,O-(1,1′-binaphthyl)dioxophosphite)-β-d-glucofuranoseC38H40O8PEe ⩾99%[α]D25=+358.5 (c 1.00, THF)Source of chirality: d-glucose and BINOLAbsolute configuration: (1R,2R,3R,4R,5R,Sa)
1,2:5,6-Di-O-isopropylidene-3-O-((S)-2,2′-O,O-(3,3′-diphenyl-1,1′-binaphthyl)dioxophosphite)-d-glucoseC44H40O8PEe ⩾99%[α]D25=+350.0 (c 0.86, THF)Source of chirality: d-glucose and BINOLAbsolute configuration: (1R,2R,3S,4R,5R,Sa)
