The synthetic versatility of alkoxycarbonyl- and hydroxymethyl-piperazine-2,5-diones

Alkoxycarbonylpiperazine-2,5-diones are versatile precursors for the α-functionalisation of piperazine-2,5-diones. The alkoxycarbonyl group activates the α-carbon position to alkylation reactions and this provides a mild and selective method for the extension of the carbon framework of piperazine-2,...

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Bibliographic Details
Published in:Tetrahedron 2005-09, Vol.61 (36), p.8722-8739
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:Alkoxycarbonylpiperazine-2,5-diones are versatile precursors for the α-functionalisation of piperazine-2,5-diones. The alkoxycarbonyl group activates the α-carbon position to alkylation reactions and this provides a mild and selective method for the extension of the carbon framework of piperazine-2,5-diones. In addition, the alkoxycarbonyl group can be converted to the carboxy group, which in turn can be ‘deleted’ or manipulated for the installation of carbon and/or heteroatom substituents where desired, the latter via N-acyliminium chemistry. We also demonstrate that hydroxymethylpiperazine-2,5-diones complement carboxypiperazinediones as precursors for the generation of N-acyliminium ions. Alkoxycarbonyl- and hydroxymethyl-piperazine-2,5-diones are versatile precursors for the α-functionalisation of piperazine-2,5-diones.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.06.084