Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst
| Title | Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst |
| Publication Type | Journal Article |
| Year of Publication | 2020 |
| Authors | Awasthi, A, Mukherjee, A, Singh, M, Rathee, G, Vanka, K, Chandra, R |
| Journal | Tetrahedron |
| Volume | 76 |
| Issue | 23 |
| Pagination | 131223 |
| Date Published | JUN |
| Type of Article | Article |
| ISSN | 0040-4020 |
| Keywords | DFT studies, Diphenylglycouril, N-tert butoxycarbonylation, organocatalyst, Proton shuttle mechanism |
| 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. (C) 2020 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2020.131223 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.233 |
Divison category:
Physical and Materials Chemistry