| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344368 | Tetrahedron: Asymmetry | 2011 | 9 Pages |
A novel class of chiral multifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a primary amino group were designed and prepared. The thioureas were proven to be effective for catalyzing the asymmetric Michael addition between isobutyraldehyde and maleimides with only 0.5 mol % catalyst loading, and exhibited double asymmetric induction. Both of the catalysts afforded the corresponding adduct with high to excellent yields (up to 98%) and excellent enantioselectivities (up to 99%). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained at the same level.
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Ethyl ent-16β-aminobeyeran-19-oateC22H37NO2[α]D20=-47.4 (c 1.0, CHCl3)Source of chirality: Ethyl ent-16β-aminobeyeran-19-oateAbsolute configuration: (4R,8R,10S,13S,16R)
Ethyl ent-16β-isothiocyanobeyeran-19-oateC23H35NO2S[α]D20=-26.5 (c 1.0, CHCl3)Source of chirality: Ethyl ent-16β-isothiocyanobeyeran-19-oateAbsolute configuration: (4R,8R,10S,13S,16R)
1-((1S,2S)-2-Aminocyclohexyl)-3-(Ethyl ent-beyeran-19-oate-16-yl)thioureaC29H49N3O2S[α]D20=-108.0 (c 1.0, CHCl3)Source of chirality: Ethyl ent-16β-aminobeyeran-19-oate 1,2-diaminocyclohexaneAbsolute configuration: (4R,8R,10S,13S,16R), (1’S,2’S)
1-((1R,2R)-2-Aminocyclohexyl)-3-(ethyl ent-beyeran-19-oate-16-yl)thioureaC29H49N3O2S[α]D20=+5.5 (c 1.0, CHCl3)Source of chirality: Ethyl ent-16β-aminobeyeran-19-oate 1,2-diaminocyclohexaneAbsolute configuration: (4R,8R,10S,13S,16R), (1’R,2’R)
2-(2,5-Dioxo-1-phenylpyrrolidin-3-yl)-2-methyl-propionaldehydeC14H15NO3[α]D20=-5.6 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-(1-(4-Fluorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC14H14FNO3[α]D20=-2.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-(1-(3-Chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC14H14ClNO3[α]D20=-6.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-(1-(4-Chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC14H14ClNO3[α]D20=-2.5 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-(1-(3-Bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC14H14BrNO3[α]D20=-4.4 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-(1-(4-Bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC14H14BrNO3[α]D20=-3.2 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-Methyl-2-(1-(3-nitrophenyl)-2,5-dioxopyrrolidin-3-yl)propanalC14H14N2O5[α]D20=-3.4 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-Methyl-2-(1-(4-nitrophenyl)-2,5-dioxopyrrolidin-3-yl)propanalC14H14N2O5[α]D20=-6.9 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-(2,5-Dioxo-1-p-tolylpyrrolidin-3-yl)-2-methylpropanalC15H17NO3[α]D20=-7.5 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-(1-(2,6-Dimethylphenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC16H19NO3[α]D20=-3.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-(1-(2-Methoxyphenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC15H17NO4[α]D20=+4.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
2-(1-Benzyl-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC15H17NO3[α]D20=+7.3 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
1-(2,5-Dioxo-1-phenylpyrrolidin-3-yl)cyclohexanecarbaldehydeC17H19NO3[α]D20=-6.7 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
1-(1-(4-Fluorophenyl)-2,5-dioxopyrrolidin-3-yl)cyclohexanecarbaldehydeC17H18FNO3[α]D20=-4.4 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
1-(1-(4-Methylphenyl)-2,5-dioxo-pyrrolidin-3-yl)cyclohexanecarbaldehydeC18H21NO3[α]D20=-4.7 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
1-(1-(2,6-Dimethylphenyl)-2,5-dioxopyrrolidin-3-yl)cyclohexanecarbaldehydeC19H23NO3[α]D20=-2.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
1-(1-(2-Methoxyphenyl)-2,5-dioxo-pyrrolidin-3-yl)cyclohexanecarbaldehydeC18H21NO4[α]D20=-6.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
1-(1-Benzyl-2,5-dioxo-pyrrolidin-3-yl)cyclohexanecarbaldehydeC18H21NO3[α]D20=+1.7 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(R)-2-((S)-2,5-Dioxo-1-phenylpyrrolidin-3-yl)propanalC14H13NO3[α]D20=-23.5 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R), (S)
(R)-2-((S)-2,5-Dioxo-1-phenylpyrrolidin-3-yl)hexanalC16H19NO3[α]D20=-20.4 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R), (S)
