| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348227 | Tetrahedron: Asymmetry | 2006 | 5 Pages |
Various l-prolinamides 14, prepared from l-proline and chiral β-amino alcohols, are active bifunctional catalysts for the direct nitro-Michael addition of ketones to β-nitrostyrenes. In particular, catalyst 14e prepared from l-proline and (1S,2R)-cis-1-amino-2-indanol exhibits the highest catalytic performance working in polar aprotic solvents such as NMP. High syn-diastereoselectivities (up to 94% de) and good enantioselectivities (up to 80% ee) were obtained at rt.
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(S)-N-(R)-[2-Hydroxy-1-phenylethyl]pyrrolidine-2-carboxamideC13H18N2O2[α]D20=-86.9 (c 1.0,CH2Cl2)Source of chirality: l-prolineAbsolute configuration: l,R
(2S)-N-[(1S,2R)-2,3-Dihydro-2-hydroxy-1H-inden-1-yl]pyrrolidine-2-carboxamideC14H18N2O2[α]D20=-24.4 (c 1.0, CH2Cl2)Source of chirality: l-prolineAbsolute configuration: l,1S,2R
(2S)-N-[(1R,2R)-2,3-Dihydro-2-hydroxy-1H-inden-1-yl]pyrrolidine-2-carboxamideC14H18N2O2[α]D20=+78.8 (c 1.0, CH2Cl2)Source of chirality: l-prolineAbsolute configuration: l,1R,2R
(2S)-N-[(1R,2S)-2,3-Dihydro-2-hydroxy-1H-inden-1-yl]pyrrolidine-2-carboxamideC14H18N2O2[α]D20=-6.9 (c 1.0, CH2Cl2)Source of chirality: l-prolineAbsolute configuration: l,1R,2S
(2S)-N-[(1S,2S)-2,3-Dihydro-2-hydroxy-1H-inden-1-yl]pyrrolidine-2-carboxamideC14H18N2O2[α]D20=-78.4 (c 1.0, CH2Cl2)Source of chirality: l-prolineAbsolute configuration: l,1S,2S
(2R)-N-[(1R,2S)-2,3-Dihydro-2-hydroxy-1H-inden-1-yl]pyrrolidine-2-carboxamideC14H18N2O2[α]D20=+24.6 (c 1.0, CH2Cl2)Source of chirality: l-prolineAbsolute configuration: d,1R,2S
(2S)-N-[(R)-2,3-Dihydro-1H-inden-1-yl]pyrrolidine-2-carboxamideC14H18N2O[α]D20=+23.4 (c 1.0, CH2Cl2)Source of chirality: l-prolineAbsolute configuration: l,R
(2S)-N-[(S)-2,3-Dihydro-1H-inden-1-yl]pyrrolidine-2-carboxamideC14H18N2O[α]D20=-76.4 (c 1.0, CH2Cl2)Source of chirality: l-prolineAbsolute configuration: l,S
(2S)-N-[(1S,2R)-2,3-Dihydro-2-hydroxy-1H-inden-1-yl]-N-methylpyrrolidine-2-carboxamideC15H20N2O2[α]D20=-29.0 (c 1.0, CH2Cl2)Source of chirality: l-prolineAbsolute configuration: l,1S,2R
syn-4-Methyl-6-nitro-5-p-tolylhexan-3-oneC14H19NO3Ee = 74% by HPLC on Chiralcel OD-H column[α]D20=+14.8 (c 1.0, CH2Cl2)Source of chirality: asymmetric catalysis
syn-5-(4-Chlorophenyl)-4-methyl-6-nitrohexan-3-oneC13H16ClNO3Ee = 78% by HPLC on Chiralcel OD-H column[α]D20=+5.7 (c 1.0, CH2Cl2)Source of chirality: asymmetric catalysis
syn-5-(4-Methoxyphenyl)-4-methyl-6-nitrohexan-3-oneC14H19NO4Ee = 73% by HPLC on Chiralcel OD-H column[α]D20=+18.7 (c 1.0, CH2Cl2)Source of chirality: asymmetric catalysis
syn-4-Methyl-6-nitro-5-(4-(trifluoromethyl)phenyl)hexan-3-oneC14H16F3NO3Ee = 50% by HPLC on Chiralcel OD-H column[α]D20=-4.5 (c 1.0, CH2Cl2)Source of chirality: asymmetric catalysis
syn-5-(3,5-Dichlorophenyl)-4-methyl-6-nitrohexan-3-oneC13H15Cl2NO3Ee = 73% by HPLC on Chiralcel OD-H column[α]D20=-24.4 (c 1.0, CH2Cl2)Source of chirality: asymmetric catalysis
