Unusual selectivity in the ring-opening of γ-valerolactone oxide by amines.

Zahra MazloomiFabian KallmeierSarah Kirchhecker Bernhard M Stadler Swechchha PandeyClaas SchünemannAnke SpannenbergChristian Hering-Junghans Sergey Tin Johannes G de Vries Eszter Baráth

Published in: Chemical communications (Cambridge, England) (2023)

Primary and secondary amines selectively react with the lactone moiety of γ-valerolactone oxide (GVLO). Several primary amines afforded the resulting epoxyamides with an intact epoxy group. In some cases addition of two equivalents of amine resulted in additional epoxide opening to give α,γ-dihydroxy-β-amino-amides. The selective lactone-opening in GVLO was further corroborated by DFT-studies.

Keyphrases

density functional theory
molecular docking
molecular dynamics simulations
case control