| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348229 | Tetrahedron: Asymmetry | 2006 | 8 Pages |
A recoverable dendrimeric supported prolinol was used as a catalyst in the asymmetric reduction of indanones and tetralones to give separable cis and trans isomers up to 97% ee. This method was also applied in the enantioselective synthesis of the antidepressant drug (+)-sertraline.
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(1R,3S)-3-Methyl-2,3-dihydro-1H-inden-1-olC10H12OEe = 82%[α]D27=-26.7 (c 0.95, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3S)
(1R,3R)-3-Methyl-2,3-dihydro-1H-inden-1-olC10H12OEe = 95%[α]D27=-27.3 (c 0.85, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3R)
(1R,3R)-3-Phenyl-2,3-dihydro-1H-inden-1-olC15H14OEe = 78%[α]D27=-12.4 (c 1.50, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3R)
(1R,3S)-3-Phenyl-2,3-dihydro-1H-inden-1-olC15H14OEe = 91%[α]D27=-30.8 (c 1.50, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3S)
(1R,3S)-3-Butyl-2,3-dihydro-1H-inden-1-olC13H18OEe = 80%[α]D28=-56.8 (c 0.75, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3S)
(1R,3R)-3-Butyl-2,3-dihydro-1H-inden-1-olC13H18OEe = 94%[α]D29=-34.4 (c 0.95, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3R)
(1R,3R)-3-tert-Butyl-2,3-dihydro-1H-inden-1-olC13H18OEe = 80%[α]D19=-59.1 (c 0.90, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3R)
(1R,3S)-3-tert-Butyl-2,3-dihydro-1H-inden-1-olC13H18OEe = 96%[α]D19=-57.9 (c 0.75, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3S)
(1R,3R)-3-Cyclohexyl-2,3-dihydro-1H-inden-1-olC15H20OEe = 78%[α]D23=-31.9 (c 0.80, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3R)
(1R,3S)-3-Cyclohexyl-2,3-dihydro-1H-inden-1-olC15H20OEe = 93%[α]D23=-35.9 (c 0.80, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,3S)
(1R,2R)-2-Methyl-2,3-dihydro-1H-inden-1-olC10H12OEe = 31%[α]D27=-65.5 (c 1.10, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,2R)
(1R,2S)-2-Methyl-2,3-dihydro-1H-inden-1-olC10H12OEe = 85%[α]D27=-59.4 (c 1.10, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,2S)
(1R,2R)-2-(2-Hydroxyethyl)cyclopentanolC7H14O2Ee = 50%[α]D25=-12.4 (c 0.20, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,2R)
(1R,2S)-2-(2-Hydroxyethyl)cyclopentanolC7H14O2Ee = 87%[α]D20=-35.3 (c 0.20, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,2S)
(1R,4R)-4-Phenyl-1,2,3,4-tetrahydronaphthalen-1-olC16H16OEe = 95%[α]D24=-49.4 (c 0.48, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4R)
(1R,4S)-4-Phenyl-1,2,3,4-tetrahydronaphthalen-1-olC16H16OEe = 88%[α]D24=-15.7 (c 1.10, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4S)
(1R,4R)-4-(4-Fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-olC16H15FOEe = 97%[α]D24=-8.8 (c 0.70, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4R)
(1R,4S)-4-(4-Fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-olC16H15FOEe = 94%[α]D27=-51.4 (c 1.35, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4S)
(1R,4R)-4-(4-Chlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-olC16H15ClOEe = 95%[α]D25=-56.9 (c 0.92, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4R)
(1R,4S)-4-(4-Chlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-olC16H15ClOEe = 95%[α]D25=-6.9 (c 0.92, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4S)
(1R,4S)-4-(2-Chlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-olC16H15ClOEe = 96%[α]D24=-43.4 (c 0.92, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4S)
(1R,4R)-4-(2-Chlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-olC16H15ClOEe = 94%[α]D24=-24.7 (c 0.92, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4R)
(1R,4R)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-olC16H14Cl2OEe = 97%[α]D24=-52.5 (c 1.14, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4R)
(1R,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-olC16H14Cl2OEe = 94%[α]D24=1.48 (c 1.00, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4S)
(1R,4R)-4-p-Tolyl-1,2,3,4-tetrahydronaphthalen-1-olC17H18OEe = 94%[α]D24=-46.84 (c 1.00, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4R)
(1R,4S)-4-p-Tolyl-1,2,3,4-tetrahydronaphthalen-1-olC17H18OEe = 91%[α]D25=-2.86 (c 1.15, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,4S)
(1R,2R)-2-Methyl-1,2,3,4-tetrahydronaphthalen-1-olC11H14OEe = 18%[α]D20=8.97 (c 0.95, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,2R)
(1R,2R)-2-(2-Hydroxyethyl)cyclohexanolC8H16O2Ee = 94%[α]D25=-13.2 (c 1.22, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,2R)
(1R,2S)-2-(2-Hydroxyethyl)cyclohexanolC8H16O2Ee = 88%[α]D23=-26.2 (c 0.70, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (1R,2S)
