Intramolecular carbolithiation of N-allyl-ynamides: An efficient entry to 1,4-dihydropyridines and pyridines - Application to a formal synthesis of sarizotan

Abstract

We have developed a general synthesis of polysubstituted 1,4-dihydropyridines and pyridines based on a highly regioselective lithiation/6-endo-dig intramolecular carbolithiation from readily available N-allyl-ynamides. This reaction, which has been successfully applied to the formal synthesis of the anti-dyskinesia agent sarizotan, further extends the use of ynamides in organic synthesis and further demonstrates the synthetic efficiency of carbometallation reactions. © 2012 Gati et al; licensee Beilstein-Institut.