sorry, we can't preview this file
...but you can still download ol3c01334_si_001.pdf
ol3c01334_si_001.pdf (10.84 MB)
5‑Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids
journal contribution
posted on 2023-05-26, 13:10 authored by Asmaa Habib, José J. Garrido-González, Estela Sánchez-Santos, Irene Boya del Teso, Francisca Sanz, Victoria Alcázar, Ángel L. Fuentes de Arriba, Joaquín R. MoránThe synthesis of
5-chloro-8-nitro-1-naphthoyl chloride and its
use as a protective group for amines is described. Protection is carried
out with an auxiliary amine or under mild Schotten-Baumann conditions
in high yield (>86%), while deprotection can be achieved easily
under
gentle reducing conditions due to the large steric tension between
C-1 and C-8 naphthalene substituents. The reaction has been successfully
tested in dipeptide synthesis and amino alcohols protection, and it
has proved selective for the ε-amine group of lysine.
