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Article Dans Une Revue Tetrahedron Année : 2013

Investigation of the lipase-catalysed reaction of aliphatic amines with ethyl propiolate as a route to N-substituted propiolamides

Résumé

The lipase catalysed reactions of benzyl- alcohol and amine with ethyl propiolate were optimized to favour the 1,2-addition, i. e. formation of benzyl prop-2-ynoate and N-benzyl prop-2-ynamide respectively in excellent yields. Immobilized Candida antartica lipase (CALB) was found to be the most efficient enzyme, and the reactions were performed in solvents such as tBME, dioxane or toluene. The methods were used to prepare naphthalimido substituted propiolic ester and amide in high yields.

Dates et versions

hal-04196601 , version 1 (06-09-2023)

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Simon Bonte, Ioana Otilia Ghinea, Isabelle Baussanne, Jean-Paul Xuereb, Rodica Dinica, et al.. Investigation of the lipase-catalysed reaction of aliphatic amines with ethyl propiolate as a route to N-substituted propiolamides. Tetrahedron, 2013, 69 (26), pp.5495-5500. ⟨10.1016/j.tet.2013.04.093⟩. ⟨hal-04196601⟩

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