Skip to Main content Skip to Navigation
Journal articles

1,3,5-Oxadiazine Framework by Oxygen vs. Nitrogen Trapping of an N-Acyliminium Ion Derived from N,O-bis-TMS Pyroglutamic Acid

Abstract : We report that the reaction of N,O-bis-TMS pyroglutamic acid with aldehydes, under basic or acid catalysis leads to O-bis-TMS adducts. Treatment of these N,O-acetals by TfOH affords azalactones or N,N′-substituted methylene-bis-pyroglutamic acids from the trapping of N-acyliminium species, respectively, with oxygen or nitrogen atom intramolecularly versus intermolecularly. Anodic oxidation of the amido acids, followed by diastereoselective oxa-cyclisation of new N-acyliminium salts, provides exclusively fused meso-1,3,5-oxadiazines with the stereochemistry secured by X-ray analysis. The reactivity of these skeletons under both alkaline and acid conditions was also envisioned and discussed. © 2017 Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim
Document type :
Journal articles
Complete list of metadatas

https://hal-normandie-univ.archives-ouvertes.fr/hal-02413278
Contributor : Vincent Loisel <>
Submitted on : Monday, December 16, 2019 - 10:43:16 AM
Last modification on : Monday, June 22, 2020 - 12:08:09 PM

Identifiers

Citation

A. Ghinet, C.-M. Abuhaie, G. Homerin, H. Marzag, J. Dubois, et al.. 1,3,5-Oxadiazine Framework by Oxygen vs. Nitrogen Trapping of an N-Acyliminium Ion Derived from N,O-bis-TMS Pyroglutamic Acid. ChemistrySelect, Wiley, 2017, 2 (33), pp.10654-10660. ⟨10.1002/slct.201701766⟩. ⟨hal-02413278⟩

Share

Metrics

Record views

52