| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348885 | Tetrahedron: Asymmetry | 2010 | 6 Pages |
A series of novel carbohydrate-based iminophosphinite ligands have been synthesized for the first time and successfully applied in Pd-catalyzed asymmetric allylic alkylation. The substituent effects on the catalytic reaction were also investigated, and 92% ee was achieved when the p-nitro-substituted ligand 10d was used.
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Benzyl-4,6-O-benzylidene-3-O-(diphenylphosphino)-2-deoxy-2-benzylideneamino-α-d-glucosideC39H36NO5P[α]D20=+15.9 (c 0.36, CHCl3)Source of chirality: N-acetyl-d-glucosamineAbsolute configuration: (1S,2R,3R,4S,5R)
Benzyl-4,6-O-benzylidene-3-O-(diphenylphosphino)-2-deoxy-2-(4-chlorobenzylideneamino)-α-d-glucosideC39H35ClNO5P[α]D20=+20.3 (c 0.84, CHCl3)Source of chirality: N-acetyl-d-glucosamineAbsolute configuration: (1S,2R,3R,4S,5R)
Benzyl-4,6-O-benzylidene-3-O-(diphenylphosphino)-2-deoxy-2-(4-methoxybenzylideneamino)-α-d-glucosideC40H38NO6P[α]D20=+13.5 (c 0.26, CHCl3)Source of chirality: N-acetyl-d-glucosamineAbsolute configuration: (1S,2R,3R,4S,5R)
Benzyl-4,6-O-benzylidene-3-O-(diphenylphosphino)-2-deoxy-2-(4-nitrobenzylideneamino)-α-d-glucosideC39H35N2O7P[α]D20=+21.4 (c 0.39, CHCl3)Source of chirality: N-acetyl-d-glucosamineAbsolute configuration: (1S,2R,3R,4S,5R)
Benzyl-4,6-O-benzylidene-3-O-(diphenylphosphino)-2-deoxy-2-(2-trifluoromethylbenzylideneamino)-α-d-glucosideC27H26NO5P[α]D20=+16.5 (c 0.50, CHCl3)Source of chirality: N-acetyl-d-glucosamineAbsolute configuration: (1S,2R,3R,4S,5R)
Benzyl-4,6-O-benzylidene-3-O-(diphenylphosphino)-2-deoxy-2-(3-chlorobenzylideneamino)-α-d-glucosideC39H35ClNO5P[α]D20=+18.7 (c 0.56, CHCl3)Source of chirality: N-acetyl-d-glucosamineAbsolute configuration: (1S,2R,3R,4S,5R)
Benzyl-4,6-O-benzylidene-3-O-(diphenylphosphino)-2-deoxy-2-(3-nitrobenzylideneamino)-α-d-glucosideC39H35N2O7P[α]D20=+21.5 (c 0.37, CHCl3)Source of chirality: N-acetyl-d-glucosamineAbsolute configuration: (1S,2R,3R,4S,5R)
