Unusual selectivity in the ring-opening of γ-valerolactone oxide by amines
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Mazloomi, Zahra
Kallmeier, Fabian
Kirchhecker, Sarah
Stadler, Bernhard M.
Pandey, Swechchha
Schünemann, Claas
Spannenberg, Anke
Hering-Junghans, Christian
Tin, Sergey
de Vries, Johannes G.
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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.
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Chemical Communications
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