Lipase-Catalyzed Aza-Michael Reaction on Acrylate Derivatives

• 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

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.