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

International audience 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 fo...

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Bibliographic Details
Published in:Tetrahedron
Main Authors: Bonte, Simon, Ghinea, Ioana Otilia, Baussanne, Isabelle, Xuereb, Jean-Paul, Dinica, Rodica, Demeunynck, Martine
Other Authors: Département de pharmacochimie moléculaire (DPM), Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes (UGA), Dunărea de Jos University of Galați Romania
Format: Article in Journal/Newspaper
Language:English
Published: HAL CCSD 2013
Subjects:
activated alkyne
transesterification
3 aminolysis
lipase
candida antartica
[CHIM.ORGA]Chemical Sciences/Organic chemistry
[CHIM.CATA]Chemical Sciences/Catalysis
antartic*
Online Access:https://hal.science/hal-04196601
https://doi.org/10.1016/j.tet.2013.04.093
Description
Summary:International audience 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.

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