کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1350415 980441 2007 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Enantioselective synthesis of heterocyclic β-aminoalcohols catalysed by a samarium iodo binaphtholate
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Enantioselective synthesis of heterocyclic β-aminoalcohols catalysed by a samarium iodo binaphtholate
چکیده انگلیسی

Enantioselective aminolysis of meso-epoxides including a heterocycle catalysed by a samarium iodo binaphtholate has been studied. New β-amino alcohols have been isolated with enantiomeric excesses up to 70%.

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(1R,2R)-4-Oxa-2-(2-methoxyphenylamino)cyclopentanolC11H15NO3Ee = 48% by HPLC on WHELK O1 column[α]D20=+7.9 (c 1.0, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (1R,2R)

(1R,2R)-4-Oxa-2-(4-methoxyphenylamino)cyclopentanolC11H15NO3Ee = 66% by HPLC on CHIRALPAK AD column[α]D20=+8.1 (c 1.0, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (1R,2R)

(3R,4R)-Benzyl 3-hydroxy-4-(2-methoxyphenylamino)pyrrolidine-1-carboxylateC19H22N2O4Ee = 43% by HPLC on CHIRALPAK AD column[α]D20=+12.1 (c 1.0, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (3R,4R)

(3R,4R)-Benzyl 3-hydroxy-4-(4-methoxy-phenylamino)pyrrolidine-1-carboxylateC19H22N2O4Ee = 10% by HPLC on CHIRALCEL OD-H column[α]D20=+3.0 (c 1.0, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (3R,4R)

(3R,4R)-tert-Butyl 3-hydroxy-4-(2-methoxyphenylamino)pyrrolidine-1-carboxylateC16H24N2O4Ee = 58% by HPLC on CHIRALPAK IA column[α]D20=+11.4 (c 1.0, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (3R,4R)

(3R,4R)-tert-Butyl 3-hydroxy-4-(4-methoxyphenylamino)pyrrolidine-1-carboxylateC16H24N2O4Ee = 47% by HPLC on CHIRALPAK IA column[α]D20=+7.5 (c 0.94, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (3R,4R)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 18, Issue 21, 22 October 2007, Pages 2598–2605
نویسندگان
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