| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349012 | Tetrahedron: Asymmetry | 2010 | 7 Pages |
A new class of β-amino alcohol and diamine ligands was prepared from isosorbide as a chiral renewable resource. The original wedge-shaped structure of isosorbide offers an interesting chiral pocket to promote the metal-catalyzed enantioselective reduction of ketones by transfer hydrogenation.
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(3S,3aR,6R,6aR)-6-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-olC13H16O4[α]D25=+109.4 (c 0.83, CHCl3)Source of chirality: isosorbideAbsolute configuration: (3S,3aR,6R,6aR)
(3R,3aR,6S,6aS)-3-(Benzyloxy)hexahydrofuro[3,2-b]furan-6-yl benzenesulfonateC19H20O6S[α]D25=+92.7 (c 0.25, CHCl3)Source of chirality: isosorbideAbsolute configuration: (3R,3aR,6S,6aS)
2-((3R,3aS,6R,6aR)-3-(Benzyloxy)hexahydrofuro[3,2-b]furan-6-ylamino)ethanolC15H21NO4[α]D25=+123.1 (c 1.1, CHCl3)Source of chirality: isosorbideAbsolute configuration: (3R,3aS,6R,6aR)
(S)-2-((3R,3aS,6R,6aR)-3-(Benzyloxy)hexahydrofuro[3,2-b]furan-6-ylamino)-3-methylbutan-1-olC18H27NO4[α]D25=+115.6 (c 1.05, CHCl3)Source of chirality: isosorbide and (S)-2-amino-3-methyl-butan-1-olAbsolute configuration: (S),(3R,3aS,6R,6aR)
(R)-2-((3R,3aS,6R,6aR)-3-(Benzyloxy)hexahydrofuro[3,2-b]furan-6-ylamino)-3-methylbutan-1-olC18H27NO4[α]D25=+136.16 (c 1.0, CHCl3)Source of chirality: isosorbide and (R)-2-amino-3-methylbutan-1-olAbsolute configuration: (R),(3R,3aS,6R,6aR)
(R)-2-((3R,3aS,6R,6aR)-3-(Benzyloxy)hexahydrofuro[3,2-b]furan-6-ylamino)-2-phenylethanolC21H25NO4[α]D25=+178.15 (c 0.5, CHCl3)Source of chirality: isosorbide and (R)-2-amino-2-phenylethanolAbsolute configuration: (R),(3R,3aS,6R,6aR)
(S)-2-((3R,3aS,6R,6aR)-3-(Benzyloxy)hexahydrofuro[3,2-b]furan-6-ylamino)-2-phenylethanolC21H25NO4[α]D25=+61.7 (c 1.0, CHCl3)Source of chirality: isosorbide and (S)-2-amino-2-phenylethanolAbsolute configuration: (S),(3R,3aS,6R,6aR)
(R)-2-((3R,3aS,6R,6aR)-3-(Benzyloxy)hexahydrofuro[3,2-b]furan-6-ylamino)-1-phenylethanolC21H25NO4[α]D25=+99.4 (c 0.5, CHCl3)Source of chirality: isosorbide and (R)-2-amino-1-phenylethanolAbsolute configuration: (R),(3R,3aS,6R,6aR)
(S)-2-((3R,3aS,6R,6aR)-3-(Benzyloxy)hexahydrofuro[3,2-b]furan-6-ylamino)-1-phenylethanolC21H25NO4[α]D25=+181.0 (c 0.5, CHCl3)Source of chirality: isosorbide and (S)-2-amino-1-phenylethanolAbsolute configuration: (S),(3R,3aS,6R,6aR)
2-((3R,3aS,6R,6aR)-3-(Benzyloxy)hexahydrofuro[3,2-b]furan-6-ylamino)-1,1-diphenylethanolC27H29NO4[α]D25=+67.5 (c 0.5, CHCl3)Source of chirality: isosorbideAbsolute configuration: (3R,3aS,6R,6aR)
(3R,3aR,6R,6aS)-N-Benzyl-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-amineC20H23NO3[α]D25=+145.3 (c 1.47, CHCl3)Source of chirality: isosorbideAbsolute configuration: (3R,3aR,6R,6aS)
(3R,3aR,6R,6aR)-6-Aminohexahydrofuro[3,2-b]furan-3-olC6H11NO3[α]D25=+110.9 (c 0.5, CH3OH)Source of chirality: isosorbideAbsolute configuration: (3R,3aR,6R,6aR)
(3R,3aR,6R,6aR)-6-(2-Hydroxyethylamino)hexahydrofuro[3,2-b]furan-3-olC8H15NO4[α]D25=+106.95 (c 0.5, CH3OH)Source of chirality: isosorbideAbsolute configuration: (3R,3aR,6R,6aR)
(3R,3aR,6R,6aR)-6-((R)-1-Hydroxy-3-methylbutan-2-ylamino)hexahydrofuro[3,2-b]furan-3-olC11H21NO4[α]D25=+81.8 (c 0.75, CH3OH)Source of chirality: isosorbide and (R)-2-amino-3-methyl-butan-1-olAbsolute configuration: (3R,3aR,6R,6aR),(R)
(3R,3aR,6R,6aS)-N-(2-Aminoethyl)-6-(benzyloxy)-hexahydrofuro[3,2-b]furan-3-amineC15H22N2O3[α]D25=+135.4 (c 1.02, CHCl3)Source of chirality: isosorbideAbsolute configuration: (3R,3aR,6R,6aS)
(3R,3aR,6R,6aS)-6-(Benzyloxy)-hexahydrofuro-N-(2-(tosylamino)ethyl)furo[3,2-b]furan-3-amineC22H28N2O5S[α]D25=+97.3 (c 1, CHCl3)Source of chirality: isosorbideAbsolute configuration: (3R,3aR,6R,6aS)
