Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives

The Candida antarctica lipase B (Novozym 435) is found to catalyze a novel decarboxylative Michael addition in vinylogous carbamate systems for the synthesis of 1,4-benzoxazinone derivatives. The reaction goes through Michael addition, ester hydrolysis and decarboxylation. A possible mechanism is su...

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Bibliographic Details
Published in:Scientific Reports
Main Authors: Bavandi, Hossein, Shahedi, Mansour, Habibi, Zohreh, Yousefi, Maryam, Brask, Jesper, Mohammadi, Mehdi
Format: Text
Language:English
Published: Nature Publishing Group UK 2022
Subjects:
Article
Antarc*
Antarctica
Online Access:http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9325775/
http://www.ncbi.nlm.nih.gov/pubmed/35882869
https://doi.org/10.1038/s41598-022-16291-3
Description
Summary:The Candida antarctica lipase B (Novozym 435) is found to catalyze a novel decarboxylative Michael addition in vinylogous carbamate systems for the synthesis of 1,4-benzoxazinone derivatives. The reaction goes through Michael addition, ester hydrolysis and decarboxylation. A possible mechanism is suggested, with simultaneous lipase-catalyzed Michael addition and ester hydrolysis. The present methodology offers formation of complex products through multi-step reactions in a one pot process under mild and facile reaction conditions with moderate to high yields (51–90%) and no side product formation. The reaction seems to be is a great example of enzymatic promiscuity.

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