کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1349570 980405 2009 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Diastereoselective Diels–Alder cycloaddition of [(1R)-10-(N,N-diethylsulfamoyl)isobornyl] 2H-azirine to nucleophilic 1,4-disubstituted 1,3-dienes
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Diastereoselective Diels–Alder cycloaddition of [(1R)-10-(N,N-diethylsulfamoyl)isobornyl] 2H-azirine to nucleophilic 1,4-disubstituted 1,3-dienes
چکیده انگلیسی

Chiral [(1R)-10-(N,N-diethylsulfamoyl)isobornyl] 2H-azirine 1 [Timén, A. S.; Somfai, P. J. Org. Chem.2003, 9958–9963; Timén, A. S.; Fisher, A.; Somfai, P. Chem. Commun.2003, 1150–1151]. was combined to a number of 1,4-disubstituted-2-aza-1,3-dienes 2a–g [Alves, M. J.; Durães, M. M.; Gil Fortes, A. Tetrahedron2004, 6541–6553] to give cycloadducts 8a–g as major isomers. High to good diastereofacial differentiation of the two faces of the azirine is observed when R1,R2 = Ar 2a–e; diastereoselectivity drops drastically when R1 = Me or H 2f,g. Cycloaddition of the azirine 1 to E,E-1,4-diacetoxy-1,3-butadiene shows complete diastereoselectivity giving cycloadduct 11a.

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[(1R)-10-(N,N-Diethylsulfamoyl)isobornyl] (6S)-4-oxo-2,5-diphenyl-1,3-diazabicyclo[4.1.0]heptane-6-carboxylateC32H41N3O5S[α]D20=+0.14 (c 5.71 g/100 ml, CH2Cl2)Absolute configuration: (1R,6S)

[(1R)-10-(N,N-Diethylsulfamoyl)isobornyl] (6S)-2-methoxyphenyl-4-oxo-5-phenyl-1,3-diazabicyclo[4.1.0]heptane-6-carboxylateC33H44N3O6SImpure 8b; Diastereomeric ratio 8:9 (3.2: 1)[α]D20=-30.0 (c 0.60 g/100 ml, CH2Cl2)Absolute configuration: (1R,6S)

[(1R)-10-(N,N-Diethylsulfamoyl)isobornyl] (6S)-2-furyl-4-oxo-5-phenyl-1,3-diazabicyclo[4.1.0]heptane-6-carboxylateC30H39N3NaO6S[α]D20=-4.7 (c 4.00 g/100 ml, CH2Cl2)Absolute configuration: (1R,6S)

[(1R)-10-(N,N-Diethylsulfamoyl)isobornyl] (6S)-5-methoxyphenyl-4-oxo-2-phenyl-1,3-diazabicyclo[4.1.0]heptane-6-carboxylateC33H43N3NaO6SImpure 8d; Diastereomeric ratio 8:9 (11.0: 1)[α]D20=-19.8 (c 0.33 g/100 ml, CH2Cl2)Absolute configuration: (1R,6S)

[(1R)-10-(N,N-Diethylsulfamoyl)isobornyl] (6S)-5-(4-fluorophenyl)-4-oxo-2-phenyl-1,3-diazabicyclo[4.1.0]heptane-6-carboxylateC32H40FN3NaO5SImpure 8e; Diastereomeric ratio 8:9 (5.7: 1)[α]D20=-45.0 (c 0.40 g/100 ml, CH2Cl2)Absolute configuration: (1R,6S)

[(1R)-10-(N,N-Diethylsulfamoyl)isobornyl] (6S)-2-methyl-4-oxo-5-phenyl-1,3-diazabicyclo[4.1.0]heptane-6-carboxylateC27H40N3O5SImpure 8f; Diastereomeric ratio 8:9 (1.5: 1)[α]D20=-51.7 (c 0.13 g/100 ml, CH2Cl2)Absolute configuration: (1R,6S)

[(1R)-10-(N,N-Diethylsulfamoyl)isobornyl] (6S)-4-oxo-5-phenyl-1,3-diazabicyclo[4.1.0]heptane-6-carboxylateC26H38N3O5SImpure 8g; Diastereomeric ratio 8:9 (3.0: 1)[α]D20=-59.6 (c 0.09 g/100 ml, CH2Cl2)Absolute configuration: (1R,6S)

[(1R)-10-(N,N-Diethylsulfamoyl)isobornyl] (6R)-4-oxo-5-phenyl-1,3-diazabicyclo[4.1.0]heptane-6-carboxylateC26H38N3O5S[α]D20=-77.5 (c 2.00 g/100 mL, CH2Cl2)Absolute configuration: (1R,6R)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 20, Issue 12, 2 July 2009, Pages 1378–1382
نویسندگان
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