2005
Deprotection
O 0345
Mild and Selective Deprotection of Carbamates with Bu4NF. — The cleavage of
aliphatic, allylic, benzylic, and phenyl carbamates, protecting different kinds
06- 068 various
of nitrogen, by Bu4NF in THF is studied. Phenyl carbamates are very easily cleaved
except for secondary aromatic amines. For tryptamine derivatives (IX) and (XI) bearing
two protected nitrogen atoms, selective cleavage is observed. The presence of an aliphatic or vinylic methyl ester function seems to inhibit the carbamate cleavage and
hydrolysis to the corresponding acids occurs. — (JACQUEMARD, U.; BENETEAU,
V.; LEFOIX, M.; ROUTIER, S.; MEROUR, J.-Y.; COUDERT*, G.; Tetrahedron 60
(2004) 44, 10039-10047; Inst. Chim. Org. Anal., CNRS, Fac. Sci., Univ. Orleans,
F-45067 Orleans, Fr.; Eng.) — Klein
2005