کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1346190 980247 2013 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Calixarene-based chiral primary amine thiourea promoted highly enantioselective asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Calixarene-based chiral primary amine thiourea promoted highly enantioselective asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides
چکیده انگلیسی

Calix[4]arene based chiral bifunctional thiourea-primary amines have been shown to act as effective catalysts for the Michael addition of aldehydes to maleimides for the first time. The corresponding adducts were generally obtained preferentially in (R)- or (S)-forms with high yields (up to 99%) and with high to excellent enantioselectivities (up to 98% ee).

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25,27-Bis[1-((1S,2S)-2--(1,3-dioxoisoindolin-2-yl)cyclohexyl)-3-propoxy)thiourea]-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl)-calix[4]areneC80H98N6O4S2[α]D25=-2.7 (c 0.6, CHCl3)Source of chirality: (1S,2S) cyclohexane-1,2-diamineAbsolute configuration: (S,S,S,S)

1-(2-(4-tert-Butylphenoxy)ethyl)-3-((1S,2S)-2-(1,3-dioxoisoindolin-2-yl)cyclohexyl)thioureaC27H33N3O3S[α]D25=-2.1 (c 0.6, CHCl3)Source of chirality: (1S,2S) cyclohexane-1,2-diamineAbsolute configuration: (S,S)

25,27-Bis[1-((1S,2S)-2-aminocyclohexyl)-3-propoxy)thiourea]-26,28-dihyd-roxy-5,11,17,23-tetra(tert-butyl)-calix[4]areneC64H94N6O4S2[α]D25=-4.9 (c 0.9, CHCl3)Source of chirality: (1S,2S) cyclohexane-1,2-diamineAbsolute configuration: (S,S,S,S)

1-((1S,2S)-2-Aminocyclohexyl)-3-(2-(4-tert-butylphenoxy)ethyl)thioureaC19H31N3OS[α]D25=-1.1 (c 2.0, CHCl3)Source of chirality: (1S,2S) cyclohexane-1,2-diamineAbsolute configuration: (S,S)

(S)-2-(2,5-Dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropanalC14H15NO3[α]D25=-3.2 (c 0.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-Methyl-2-(1-(4-nitrophenyl)-2,5-dioxopyrrolidin-3-yl)propanalC14H14N2O5[α]D25=-2.9 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-(1-Benzyl-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC15H17NO3[α]D25=+11.9 (c 0.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-(1-(4-Chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC14H14ClNO3[α]D25=-2.4 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-(1-(4-Bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanalC14H14BrNO3[α]D25=-3.1 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(2,5-Dioxo-1-phenylpyrrolidin-3-yl)cyclohexanecarbaldehydeC17H19NO3[α]D25=-0.7 (c 0.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(1-Benzyl-2,5-dioxopyrrolidin-3-yl)cyclohexanecarbaldehydeC18H21NO3[α]D25=+1.6 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(2,5-Dioxo-1-phenylpyrrolidin-3-yl)cyclopentanecarbaldehydeC16H17NO3[α]D25=+18.2 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(1-Benzyl-2,5-dioxopyrrolidin-3-yl)cyclopentanecarbaldehydeC17H19NO3[α]D25=-0.7 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(1-(4-Bromophenyl)-2,5-dioxopyrrolidin-3-yl)cyclopentanecarbaldehydeC16H16BrNO3[α]D25=+1.9 (c 0.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(1-(4-Nitrophenyl)-2,5-dioxopyrrolidin-3-yl)cyclopentanecarbaldehydeC16H16N2O5[α]D25=+2.3 (c 0.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(1-(4-Chlorophenyl)-2,5-dioxopyrrolidin-3-yl)cyclopentanecarbaldehydeC16H16ClNO3[α]D25=+1.9 (c 1.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-(2,5-Dioxo-1-phenylpyrrolidin-3-yl)-2-ethylbutanalC16H19NO3[α]D25=-6.3 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-(1-(4-Bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-ethylbutanalC16H18BrNO3[α]D25=-2.1 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-(1-Benzyl-2,5-dioxopyrrolidin-3-yl)-2-ethylbutanalC17H21NO3[α]D25=-2.9 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-Ethyl-2-(1-(4-Nitrophenyl)-2,5-dioxopyrrolidin-3-yl)butanalC16H18N2O5[α]D25=-1.7 (c 0.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-(1-(4-Chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-ethylbutanalC16H18ClNO3[α]D25=-1.9 (c 0.7, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-(2,5-Dioxo-1-phenylpyrrolidin-3-yl)-2-methylpentanalC16H19NO3[α]D25=-1.3 (c 0.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 24, Issue 23, 15 December 2013, Pages 1443–1448
نویسندگان
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