| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347620 | Tetrahedron: Asymmetry | 2008 | 6 Pages |
A new series of tridentate P,N,O ligands having hard and soft donor atoms derived from chiral amino alcohols were developed and employed in the Cu(II)-catalyzed conjugate addition of diethylzinc to substituted chalcones. The asymmetric additions to a variety of substituted chalcones afforded products in excellent yields and good to excellent enantioselectivities up to 97% ee.
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(S)-2-(2-(Diphenylphosphino)benzylideneamino)-3-phenylpropan-1-olC28H26NOP[α]D25=-117 (c 1, CH2Cl2)Absolute configuration: (S)Source of chirality: l-phenylalanine as starting material
(1R,2S)-2-[2-(Diphenylphosphino)benzylideneamino]-1,3-diphenylpropan-1-olC34H30NOP[α]D25=-87.5 (c 1, CH2Cl2)Absolute configuration: (1R,2S)Source of chirality: l-phenylalanine as starting material
(S)-2-(2-(Diphenylphosphino)benzylideneamino)-1,1,3-triphenylpropan-1-olC40H34NOP[α]D25=-83.5 (c 1, CH2Cl2)Absolute configuration: (S)Source of chirality: l-phenylalanine as starting material
(S)-2-(2-(Diphenylphosphino)benzylideneamino)-3-methyl-1,1-diphenylbutan-1-olC36H34NOP[α]D25=-16.05 (c 1, CH2Cl2)Absolute configuration: (S)Source of chirality: l-valine as starting material
1-(2-Methoxyphenyl)-3-phenylpentan-1-oneC18H20O2Ee = 81%[α]D25=-16.05 (c 1, CH2Cl2)
1-(3-Methoxyphenyl)-3-phenyl-pentan-1-oneC18H20O2Ee = 85%[α]D25=-16.0 (c 1, CH2Cl2)
1-(4-Methoxyphenyl)-3-phenyl-pentan-1-oneC18H20O2Ee = 80%[α]D25=-21.65 (c 1, CH2Cl2)
3-(2-Methoxyphenyl)-1-phenyl-pentan-1-oneC18H20O2Ee = 96%[α]D25=-11.7 (c 1, CH2Cl2)
3-(3-Methoxyphenyl)-1-phenyl-pentan-1-oneC18H20O2Ee = 78%[α]D25=-5.3 (c 1, CH2Cl2)
3-(4-Methoxyphenyl)-1-phenyl-pentan-1-oneC18H20O2Ee = 84%[α]D25=-14.3 (c 1, CH2Cl2)
3-(2-Methoxyphenyl)-1-(3-methoxyphenyl)-pentan-1-oneC19H22O3Ee = 97%[α]D25=-9.05 (c 1, CH2Cl2)
3-(2-Methoxyphenyl)-1-(4-methoxyphenyl)-pentan-1-oneC19H22O3Ee = 93%[α]D25=-10.1 (c 1, CH2Cl2)
3-(2-Bromophenyl)-1-phenyl-pentan-1- oneC17H17BrOEe = 96%[α]D25=-35.7 (c 1, CH2Cl2)
3-(2-Chlorophenyl)-1-phenyl-pentan-1-oneC17H17ClOEe = 96%[α]D25=-32.5 (c 1, CH2Cl2)
3-(2-Bromophenyl)-1-(3-methoxyphenyl)pentan-1-oneC18H19BrO2Ee = 95%[α]D25=-33.8 (c 1, CH2Cl2)
3-(2-Bromophenyl)-1-(4-methoxyphenyl)pentan-1-oneC18H19BrO2Ee = 94%[α]D25=-39.3 (c 1, CH2Cl2)
3-(2-Chlorophenyl)-1-(3-methoxyphenyl)pentan-1-oneC18H19ClO2Ee = 97%[α]D25=-33.0 (c 1, CH2Cl2)
3-(2-Chlorophenyl)-1-(4-methoxyphenyl)pentan-1-oneC18H19ClO2Ee = 94%[α]D25=-38.6 (c 1, CH2Cl2)
