Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst

• DOI: 10.1016/j.tet.2020.131223
• Publication Date: 2020-04-29T15:27:06Z
• Authors: Amardeep Awasthi; Anagh Mukherjee; Mandeep Singh; Garima Rathee; Kumar Vanka; Ramesh Chandra
• Keywords: Isocyanate; Reusability

Abstract An efficient approach for the Chemoselective N-tert-butoxycarbonylation of a variety of amines using diphenylglycoluril as organocatalyst has been described. For the first time, a plausible mechanism for the N-tert-butoxycarbonylation has been proposed using density functional theory (DFT) calculations supported by NMR studies. The reusability of the organocatalyst and observation of the desired N-Boc protected amines being formed without the formation of side products like urea, oxazolidinone, isocyanate, and N, N-di-Boc derivatives makes the present protocol desirable.