Controlled Ring Opening of N-Sulfinyl- and N-Silyl-N-carboxyanhydrides (NCA)

One-Pot Synthesis of Dipeptides and Unsymmetrical Peptidyl Ureas from Unprotected NCA, Synthesis of Dipeptides and Unsymmetrical Peptidyl Ureas

Julia Mateos-Caro, Yves Robin, Vincent Levacher,* Francis Marsais , Synlett 2009 pp 279-283


Keywords

N-protected carboxyanhydrides (NCA) - peptidyl ­ureas - dipeptides

Abstract

We report herein new labile protecting groups of N-carboxyanhydrides (NCA) useful to prevent polymerization during coupling reactions with nitrogen nucleophiles. Thus, N-sulfinyl-NCA 1 and N-silyl-NCA 2 were prepared in situ and involved, without being isolated, in coupling reactions with various α-amino esters to furnish dipeptides 3 and unsymmetrical peptidyl ureas 4, respectively, in good yields.