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

Abstract 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 mechan...

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Bibliographic Details
Published in:Scientific Reports
Main Authors: Hossein Bavandi, Mansour Shahedi, Zohreh Habibi, Maryam Yousefi, Jesper Brask, Mehdi Mohammadi
Format: Article in Journal/Newspaper
Language:English
Published: Nature Portfolio 2022
Subjects:
Medicine
R
Science
Q
Antarc*
Antarctica
Online Access:https://doi.org/10.1038/s41598-022-16291-3
https://doaj.org/article/c3ecb44a8c2f4d7c8e760622b80aa245
Description
Summary:Abstract 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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