768381-45-9Relevant academic research and scientific papers
Enantio- and diastereoselective synthesis of 2,5-disubstituted pyrrolidines through a multicomponent Ugi reaction and their transformation into bicyclic scaffolds
Banfi, Luca,Basso, Andrea,Guanti, Giuseppe,Riva, Renata
, p. 6637 - 6640 (2007/10/03)
2,5-Disubstituted pyrrolidines 2a,b have been prepared from L-glutamic acid by a diastereoselective Ugi condensation on pyrroline 1. Intermediates 2a,b have been converted into diastereomeric bicyclic lactones 3a,b. A new enantio- and diastereoselective synthesis of 2,5-disubstituted pyrrolidines through a multicomponent approach has been developed, using highly reactive pyrrolines 4 as preformed cyclic imines. The pyrrolidines obtained using protected aspartic acid as acid component in the Ugi condensation have been transformed into two epimeric bicyclic lactones 18, 19, which may find an application as external reverse turn inducers.
