PAPER: Catalytic asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides – a simple approach to optically active highly functionalized proline derivatives

Gothelf, A. S.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A.

Angew. Chem. Int. Ed. 2002, 41, 4236–4238, doi: 10.1002/1521-3773(20021115)41:22<4236::AID-ANIE4236>3.0.CO;2-W

Danish National Research Foundation: Center for Catalysis Department of Chemistry, Aarhus University 8000 Aarhus C, Denmark


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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