A new selective cleavage of n,n-dicarbamoyl-protected amines using lithium bromide.
A mild and new procedure for the selective cleavage of an alkoxycarbonyl group (Boc, CBz) in N,N-dicarbamoyl-protected amino compounds is described. The method is based on the use of lithium bromide in acetonitrile and is compatible with a large range of other functionalities present in the substrates. Compared with other reported methodologies, the procedure is particularly useful for the Cbz-selective cleavage in N,N-Ts,Cbz-diprotected amines. A rationalization of the selectivity supported by ab initio calculations is also presented.
Hernández
J Nicolás
JN
Instituto Universitario de Bio-Orgánica, Universidad de La Laguna, C/Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.
Ramírez
Miguel A
MA
Martín
Víctor S
VS