Catalytic removal of N-allyloxycarbonyl groups using the [CpRu(IV)(pi-C3H5)(2-quinolinecarboxylato)]PF6 complex. A new efficient deprotecting method in peptide synthesis.
A variety of amines including even sterically less demanding and highly nucleophilic secondary amines have been efficiently deprotected without decarboxylative N-allylation from the corresponding N-allyloxycarbonyl (N-AOC) compounds by using a catalytic amount of [CpRu(IV)(pi-C3H5)(2-quinolinecarboxylato)]PF6 in the presence of 1 molar amount of trifluoromethanesulfonic acid, the general utility of which has been demonstrated by the efficient synthesis of a collagen protein unit tripeptide, Pro-Pro-Gly.
Tanaka
Shinji
S
Research Center for Materials Science and Department of Chemistry, Nagoya University, Japan.
Saburi
Hajime
H
Murase
Takanori
T
Yoshimura
Masahiro
M
Kitamura
Masato
M
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003094:Collagen; D008722:Methods; D009842:Oligopeptides / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis*
D000588:Amines; D009842:Oligopeptides; D010455:Peptides; C044555:prolyl-prolyl-glycine; D003094:Collagen