کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1345151 1500346 2014 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Oxygen–chlorine interactions in the transition state of asymmetric Michael additions of carbonyl compounds to β-nitrostyrene
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Oxygen–chlorine interactions in the transition state of asymmetric Michael additions of carbonyl compounds to β-nitrostyrene
چکیده انگلیسی

An oxygen–chlorine interaction is reported in the transition state of the Michael addition of acetone to nitrostyrene catalyzed by enantioenriched monosulfonamides. The interaction between the oxygen from the nitro group and the chlorine at the ortho-position of the sulfonamide moiety is supported by theoretical calculations. Asymmetric Michael addition products catalyzed by monosulfonamides were obtained in moderate yields and enantioselectivities.

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N-((1R,2R)-2-Aminocyclohexyl)-2,3-dichlorobenzenesulfonamideC12H16Cl2N2O2S[α]D20 = −20 (c 0.72, CH2Cl2)Absolute configuration: (1R,2R)Source of chirality: (R,R)-1,2-diaminocyclohexane

N-((1R,2R)-2-Aminocyclohexyl)-2,5-dichlorobenzenesulfonamideC12H16Cl2N2O2S[α]D20 = −29 (c 1.1, MeOH)Absolute configuration: (1R,2R)Source of chirality: (R,R)-1,2-diaminocyclohexane

N-((1R,2R)-2-Aminocyclohexyl)-2,6-dichlorobenzenesulfonamideC12H16Cl2N2O2S[α]D20 = −30 (c 0.84, CH2Cl2)Absolute configuration: (1R,2R)Source of chirality: (R,R)-1,2-diaminocyclohexane

N-((1R,2R)-2-aminocyclohexyl)-2,5-dibromobenzenesulfonamideC12H16Br2N2O2S[α]D20 = −17 (c 6.1, MeOH)Absolute configuration: (1R,2R)Source of chirality: (R,R)-1,2-diaminocyclohexane

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 25, Issues 13–14, 31 July 2014, Pages 997–1001
نویسندگان
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