SCHEDULED MAINTENANCE
Unusual selectivity in the ring-opening of γ-valerolactone oxide by amines†
Sarah
Kirchhecker, 
a
Bernhard M.
Stadler,
a
Swechchha
Pandey,
a
Christian
Hering-Junghans,
a
Sergey
Tin,
a
Johannes G.
de Vries
*a
and
Eszter
Baráth
*a
a
Bernhard M.
Stadler,
a
Swechchha
Pandey,
a
Christian
Hering-Junghans,
a
Sergey
Tin,
a
Johannes G.
de Vries
*a
and
Eszter
Baráth
*a
Abstract
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.
Please wait while we load your content...
