| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346074 | Tetrahedron: Asymmetry | 2012 | 6 Pages |
The asymmetric double Michael additions of curcumins to nitroalkenes to afford highly functionalized cyclohexanones have been carried out for the first time. A combination of a dihydrocinchonine-thiourea organocatalyst and K2CO3 was found to be the most effective in obtaining the desired cyclohexanones in good yield, diastereoselectivity and enantioselectivity.
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3,5-Bis(4-methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitrocyclohexanoneC30H29NO7[α]D18=-41.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
3-(3,4-Dimethoxyphenyl)-5-(4-methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitrocyclohexanoneC31H31NO8[α]D19=-49.9 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
5-(4-Methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitro-3-(3,4,5-trimethoxyphenyl)cyclohexanoneC32H33NO9[α]D19=-47.6 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
3-(Benzo[d][1,3]dioxol-5-yl)-5-(4-methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitrocyclohexanoneC30H27NO8[α]D18=-91.2 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
5-(4-Methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitro-3-(p-tolyl)cyclohexanoneC30H29NO6[α]D21=-50.7 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
5-(4-Methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryoloyl)-4-nitro-3-phenylcyclohexanoneC29H27NO6[α]D21=-55.3 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
3-(4-Chlorophenyl)-5-(4-methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitrocyclohexanoneC29H26NO6Cl[α]D21=-104.2 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
3-(4-Bromophenyl)-5-(4-methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitrocyclohexanoneC29H26NO6Br[α]D21=-112.3 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
3-(3-Bromophenyl)-5-(4-methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitrocyclohexanoneC29H26NO6Br[α]D19=-79.4 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
5-(4-Methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitro-3-(2-nitrophenyl)cyclohexanoneC29H26N2O8[α]D19=+5.4 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
5-(4-Methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitro-3-(3-nitrophenyl)cyclohexanoneC29H26N2O8[α]D19=-18.6 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
3-(Furan-2-yl)-5-(4-methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitrocyclohexanoneC27H25NO7[α]D19=-71.5 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
5-(4-Methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitro-3-(thiophen-2-yl)cyclohexanoneC27H25NO6S[α]D18=-77.4 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
5-(3,4-Dimethoxyphenyl)-3-(4-methoxyphenyl)-2-((E)-3-(3,4-dimethoxyphenyl)acryloyl)-4-nitrocyclohexanoneC32H33NO9[α]D25=-44.3 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
3-(4-Methoxyphenyl)-4-nitro-5-phenyl-2-((E)-3-phenylacryloyl)cyclohexanoneC28H25NO5[α]D25=-40.3 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
5-(Furan-2-yl)-2-((E)-3-(furan-2-yl)-acryloyl)-3-(4-methoxyphenyl)-4-nitrocyclohexanoneC24H21NO7[α]D25=-26.6 (c 0.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: nd
