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

Primary and secondary amines selectively react with the lactone moiety of gamma-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 alpha,gamma-dihydroxy-beta-amino-amides. The selective lactone-opening in GVLO was further corroborated by DFT-studies.