Multi-purpose functionality for the structural elaboration of the piperazine-2,5-dione motif

Mild methods for controlled C- and N-alkylation of 3-benzyloxycarbonylpiperazine-2,5-diones are reported. The benzyloxylcarbonyl substituent can also serve as latent functionality for N-acyliminium ion formation and subsequent trapping enables installation of new carbon and/or heteroatom substituent...

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Bibliographic Details
Published in:Tetrahedron letters 2003-01, Vol.44 (2), p.263-265
Main Authors: Chai, Christina L.L., Elix, John A., Huleatt, Paul B.
Format: Article
Language:English
Subjects:
alkylations
amino acids and derivatives
N-acyliminium ions
trapping reactions
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Summary:Mild methods for controlled C- and N-alkylation of 3-benzyloxycarbonylpiperazine-2,5-diones are reported. The benzyloxylcarbonyl substituent can also serve as latent functionality for N-acyliminium ion formation and subsequent trapping enables installation of new carbon and/or heteroatom substituents. The use of a benzyloxycarbonyl substituent on a piperazine-2,5-dione ring to enhance and direct reactions as well as to serve as latent functionality to carbon and/or heteroatom substitution is described.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)02571-6