Affiliation:
1. Institute of Organic Chemistry Stereochemistry Research Group HUN-REN Research Centre for Natural Sciences H-1117 Budapest Magyar tudósok krt. 2 Hungary
2. Institute of Organic Chemistry MS Proteomics Research Group HUN-REN Research Centre for Natural Sciences H-1117 Budapest Magyar tudósok krt. 2 Hungary
3. Directorate of Drug Substance Development Egis Pharmaceuticals Plc. P.O. Box 100 H-1475 Budapest Hungary
Abstract
AbstractDiversity‐oriented synthesis of some novel functionalized azaheterocyclic β‐amino esters with multiple chiral centers from 1,3‐cyclooctadiene‐based β‐amino acids through a stereocontrolled synthetic route has been accomplished. The strategy was based on the creation of some novel unsaturated N‐protected cyclic β‐amino esters from 1,3‐cyclooctadiene. Products were subjected to ring‐opening metathesis (ROM) followed by selective ring‐closing metathesis (RCM). A comparative investigation on the selectivity, regarding the catalysts, yields, conversions, and substrate directing effect on ring‐rearrangement metathesis (RRM) transformation has been accomplished. Importantly, the procedure used in this synthetic process does not affect the configuration of the chiral centers. The pathway takes place across conservation of the configurations of the stereocenters; therefore, the architectural skeleton of the starting cyclooctene‐based β‐amino acids predetermined the structure of the new azaheterocyclic systems.