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

Zahra Mazloomi,Fabian Kallmeier,Sarah Kirchhecker,Bernhard M. Stadler,Swechchha Pandey, Claas Schünemann,Anke Spannenberg,Christian Hering-Junghans,Sergey Tin,Johannes G. de Vries,Eszter Baráth

Chemical communications (Cambridge, England)（2023）

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摘要

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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amines,ring-opening

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