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Article Dans Une Revue Organic Letters Année : 2017

A General Approach to the Aza-Diketomorpholine Scaffold


A stereoconservative three-step synthesis to access to 1,2,4-oxadiazine-3,6-dione is presented. This underexplored platform could be considered as a constrained oxy-azapeptide or an aza-diketomorpholine, the methodology being then successfully applied to produce enantiopure aza-analogs of diketomorpholine natural products. Importantly, the first crystal structures were obtained and compared to diketomorpholine and diketopiperazine structures. Finally, a straightforward procedure concerning the coupling of this heterocyclic scaffold with various amino acids to afford original pseudodipeptide analogs was described.


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Dates et versions

hal-03564440 , version 1 (10-02-2022)



Mathéo Berthet, Baptiste Legrand, Jean Martinez, Isabelle Parrot. A General Approach to the Aza-Diketomorpholine Scaffold. Organic Letters, 2017, 19 (3), pp.492-495. ⟨10.1021/acs.orglett.6b03656⟩. ⟨hal-03564440⟩
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