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...
Published in: | Tetrahedron |
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Main Authors: | , , , , , |
Other Authors: | , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
HAL CCSD
2013
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Subjects: | |
Online Access: | https://hal.science/hal-04196601 https://doi.org/10.1016/j.tet.2013.04.093 |
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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