Yochai Basel, A. Hassner
Apr 1, 2002
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Carboxylic acids were activated in the presence of DMAP with tert -butyl carbonates (BOC-OX) 1 , which were prepared in situ by reaction of X-OH and di- tert -butyl dicarbonate (BOC 2 O). The most efficient active carbonate proved to be tert -butyl 3-(3,4-dihydrobenzotriazine-4-on)yl carbonate 1a , leading to efficient formation of benzotriazinonyl esters 3 and 6 , which are intermediates in reactions with primary and secondary amines to afford amides or peptides in good yield. By-products in the formation of 3 or 6 are the environmentally safe tert -BuOH and CO 2 . The hindered amino acid AIB also forms a dipeptide in good yield.