The first enzyme-promoted addition of nitromethane to imines (aza-Henry reaction).

Ignacy Janicki, Piotr Łyżwa, Piotr Kiełbasiński

Bioorganic chemistry 2020 Jan

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Enzyme catalytic promiscuity is the ability of a single enzyme active site to catalyze several chemical transformations, among them those which are different from natural. We have attempted to use this feature of enzymes in the nucleophilic addition of nitromethane to aldimines (the aza-Henry reaction) whose chemically catalyzed version leads to synthetically useful β-nitroamines. We succeded in obtaining for the first time the desired products in the yields up to 81%. The most efficient proved lipase TL (from Pseudomonas stutzeri) and oxynitrilase from Arabidopsis thaliana. However, all the reactions investigated were non-stereoselective. Copyright © 2019 Elsevier Inc. All rights reserved.

Citation

Ignacy Janicki, Piotr Łyżwa, Piotr Kiełbasiński. The first enzyme-promoted addition of nitromethane to imines (aza-Henry reaction). Bioorganic chemistry. 2020 Jan;94:103377