Lanthanum(III) Trifluoromethanesulfonate Catalyzed Direct Synthesis of Ureas from N-Benzyloxycarbonyl-, N-Allyloxycarbonyl-, and N-2,2,2-Trichloroethoxycarbonyl-Protected Amines

Abstract

A novel lanthanum triflate mediated conversion of N-benzyl­oxycarbonyl-, N-allyloxycarbonyl-, and N-trichloroethoxycarbonyl-­protected amines into nonsymmetric ureas was discovered. In this study, lanthanum triflate was found to be an effective catalyst for preparing various nonsymmetric ureas from protected amines. A variety of protected aromatic and aliphatic carbamates reacted readily with various amines in the presence of lanthanum triflate to generate the desired ureas in high yields. This result demonstrated that this novel lanthanum triflate catalyzed preparation of ureas from Cbz, Alloc, and Troc carbamates can be employed for the formation of various urea structures.