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Novel Approach to 5-Substituted Proline Derivatives Using a Silver-Catalyzed Cyclization as the Key Step

2005; American Chemical Society; Volume: 70; Issue: 5 Linguagem: Inglês

10.1021/jo0484023

1520-6904

Bart C. J. van Esseveldt, Paul W. H. Vervoort, Floris L. van Delft, Floris P. J. T. Rutjes,

Chemical Synthesis and Analysis

A novel synthetic approach to the synthesis of enantiomerically pure 2,5-disubstituted pyrrolines is described. The methodology involves a Ag-catalyzed 5-endo-dig cyclization of enantiopure aryl-substituted acetylene-containing amino acids. It has also been shown that the obtained pyrrolines can be efficiently transformed into the corresponding saturated 5-aryl-substituted proline derivatives.