The 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.