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A New Selective Cleavage of N , N -Dicarbamoyl-Protected Amines Using Lithium Bromide

2002; American Chemical Society; Volume: 68; Issue: 3 Linguagem: Inglês

10.1021/jo026300b

1520-6904

J. Nicolás Hernández, Miguel Á. Ramírez, Victor S. Martı́n,

Coordination Chemistry and Organometallics

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.