| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348106 | Tetrahedron: Asymmetry | 2012 | 6 Pages |
A mixture of chiral ligand 4 [(+)-MINBOL] and Ni(acac)2 (12.5 and 0.5 mol % respectively) is able to successfully catalyze the enantioselective conjugate 1,4-addition of dialkylzinc to α,β-unsaturated enones in propionitrile to give the corresponding chiral Michael adducts in good yields and with high enantioselectivities (up to 93% ee).
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1,3-Diphenyl-1-pentanoneC17H18OEe = 92%[α]D24=+7.4 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(4-methylphenyl)-pentanoneC18H20OEe = 89%[α]D24=+14.2 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(4-methoxyphenyl)-pentanoneC18H20O2Ee = 89%[α]D24=+16.0 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(4-trifluoromethyl-phenyl)-pentanoneC18H17F3OEe = 91%[α]D24=-6.8 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(4-cyanophenyl)-pentanoneC18H17NOEe = 87%[α]D24=-17.8 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(4-flourophenyl)-pentanoneC17H17FOEe = 89%[α]D24=+5.1 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(4-chlorophenyl)-pentanoneC17H17ClOEe = 87%[α]D25=+1.4 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(4-bromophenyl)-pentanoneC17H17BrOEe = 90%[α]D24=+1.4 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(3-chlorophenyl)-pentanoneC17H17ClOEe = 92%[α]D24=-4.4 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(3-methoxyphenyl)-pentanoneC18H20O2Ee = 91%[α]D24=+5.9 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(2-methoxyphenyl)-pentanoneC18H20O2Ee = 51%[α]D24=+4.4 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-Phenyl-3-(2-chlorophenyl)-pentanoneC17H17ClOEe = 81%[α]D24=-32.0 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-(4-Methoxyphenyl)-3-phenyl-pentanoneC18H20O2Ee = 89%[α]D24=-1.6 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
1-(3-Methoxyphenyl)-3-phenyl-pentanoneC18H20O2Ee = 88%[α]D24=+11.5 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
3-Cyclohexyl-1-phenyl-pentanoneC17H24OEe = 70%[α]D26=-2.1 (c 0.5, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: R
3-Methyl-1-phenyl-pentanoneC12H16OEe = 64%[α]D24=+8.9 (c 1.0, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: S
4-Phenyl-hexan-2-oneC12H16OEe = 58%[α]D18=-19.7 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: R
1,3-Diphenyl-butanoneC16H16OEe = 80%[α]D28=+32.1 (c 2.0, CCl4)Source of chirality: asymmetric synthesisAbsolute configuration: S
1,3-Diphenyl-heptanoneC19H22OEe = 82%[α]D28=-3.4 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: S
4-Methyl-1,3-diphenyl-pentan-1-oneC18H20OEe = 7%[α]D20=+0.3 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: R
