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

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-03, Vol.70 (5), p.1791-1795
Main Authors: van Esseveldt, Bart C. J, Vervoort, Paul W. H, van Delft, Floris L, Rutjes, Floris P. J. T
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Molecular Structure
Organic chemistry
Preparations and properties
Proline - analogs & derivatives
Proline - chemical synthesis
Proline - chemistry
Silver - chemistry
Stereoisomerism
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Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0484023