Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides-A Simple Approach to Optically Active Highly Functionalized Proline Derivatives

Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides-A Simple Approach to Optically Active Highly Functionalized Proline Derivatives

Highly substituted pyrrolidines 4 are formed in a highly diastereo‐ and enantioselective 1,3‐dipolar cycloaddition reaction of azomethine ylides with electron‐deficient alkenes 2. The azomethine ylides are generated from glycinates 1 catalyzed by a chiral zinc(II) bisoxazoline catalyst 3.

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Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2002-11, Vol.41 (22), p.4236-4238
Hauptverfasser: Gothelf, Aase Sejr, Gothelf, Kurt V., Hazell, Rita G., Jørgensen, Karl Anker
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
Azo Compounds - chemistry
Catalysis
Cyclization
cycloaddition
Models, Molecular
Molecular Conformation
nitrogen heterocycles
Proline - analogs & derivatives
Proline - chemical synthesis
Stereoisomerism
ylide
zinc
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Beschreibung
Zusammenfassung:Highly substituted pyrrolidines 4 are formed in a highly diastereo‐ and enantioselective 1,3‐dipolar cycloaddition reaction of azomethine ylides with electron‐deficient alkenes 2. The azomethine ylides are generated from glycinates 1 catalyzed by a chiral zinc(II) bisoxazoline catalyst 3.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20021115)41:22<4236::AID-ANIE4236>3.0.CO;2-W