A versatile annulation protocol toward novel constrained phosphinic peptidomimetics

Magdalini Nasopoulou, Dimitris Georgiadis, Magdalini Matziari, Vincent Dive, Athanasios Yiotakis*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)


(Chemical Equation Presented) The development of a novel 3-center 2-component annulation reaction between α,ω-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting α,ω-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochemistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.

Original languageEnglish
Pages (from-to)7222-7228
Number of pages7
JournalJournal of Organic Chemistry
Issue number19
Publication statusPublished - 14 Sept 2007
Externally publishedYes

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