Lipase-Catalyzed Aza-Michael Reaction on Acrylate Derivatives

A methodology has been developed for an efficient and selective lipase-catalyzed aza-Michael reaction of various amines (primary and secondary) with a series of acrylates and alkylacrylates. Reaction parameters were tuned, and under the optimal conditions it was found that Pseudomonas stutzeri lipas...

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Bibliographic Details
Published in:The Journal of Organic Chemistry
Main Authors: Steunenberg, P., Sijm, M., Zuilhof, H., Sanders, J.P.M., Scott, E.L., Franssen, M.C.R.
Format: Article in Journal/Newspaper
Language:English
Published: 2013
Subjects:
acrylonitrile
additions
aminolysis reactions
biocatalysis
candida-antarctica
chemoselectivity
enzyme immobilization
monomers
organic-solvents
secondary-amines
Antarc*
Antarctica
Online Access:https://research.wur.nl/en/publications/lipase-catalyzed-aza-michael-reaction-on-acrylate-derivatives
https://doi.org/10.1021/jo400268u
Description
Summary:A methodology has been developed for an efficient and selective lipase-catalyzed aza-Michael reaction of various amines (primary and secondary) with a series of acrylates and alkylacrylates. Reaction parameters were tuned, and under the optimal conditions it was found that Pseudomonas stutzeri lipase and Chromobacterium viscosum lipase showed the highest selectivity for the aza-Michael addition to substituted alkyl acrylates. For the first time also, some CLEAs were examined that showed a comparable or higher selectivity and yield than the free enzymes and other formulations.

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