Daga MC,
Taddei M,
*,
Varchi G.
Università degli Studi di Sassari, Italy
Rapid Microwave-Assisted Deprotection of
N-Cbz and
N-Bn Derivatives.
Tetrahedron Lett. 2001;
42: 5191-5194
DOI:
10.1016/S0040-4039(01)00969-8
Key words
microwave heating - deprotection - palladium catalysis - hydrogenation - amines -
protecting groups
Significance
Protecting groups play an inherent role in organic synthesis, especially in peptide
chemistry. Among them, Cbz and Bn are the most popular protecting groups for amines.
Consequently, the development of methods for their installation and deprotection have
gained attention. In 2001, Taddei and co-workers developed a microwave-assisted catalytic
transfer hydrogenation for the deprotection of the N-Cbz and N-Bn derivatives.
Comment
Deprotection of N-Cbz and N-Bn of amino acids, peptides, and amines proceeds efficiently by microwave-assisted
transfer hydrogenation with Pd/C catalyst and ammonium formate reagent to afford the
corresponding free amines in good yields. This method is mild, simple, rapid, and
is also applicable to solid resin-supported substrates.
