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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Autores principales: Bavandi, Hossein, Shahedi, Mansour, Habibi, Zohreh, Yousefi, Maryam, Brask, Jesper, Mohammadi, Mehdi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9325775/
https://www.ncbi.nlm.nih.gov/pubmed/35882869
http://dx.doi.org/10.1038/s41598-022-16291-3
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author Bavandi, Hossein
Shahedi, Mansour
Habibi, Zohreh
Yousefi, Maryam
Brask, Jesper
Mohammadi, Mehdi
author_facet Bavandi, Hossein
Shahedi, Mansour
Habibi, Zohreh
Yousefi, Maryam
Brask, Jesper
Mohammadi, Mehdi
author_sort Bavandi, Hossein
collection PubMed
description 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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spelling pubmed-93257752022-07-28 Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives Bavandi, Hossein Shahedi, Mansour Habibi, Zohreh Yousefi, Maryam Brask, Jesper Mohammadi, Mehdi Sci Rep Article 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. Nature Publishing Group UK 2022-07-26 /pmc/articles/PMC9325775/ /pubmed/35882869 http://dx.doi.org/10.1038/s41598-022-16291-3 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Bavandi, Hossein
Shahedi, Mansour
Habibi, Zohreh
Yousefi, Maryam
Brask, Jesper
Mohammadi, Mehdi
Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives
title Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives
title_full Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives
title_fullStr Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives
title_full_unstemmed Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives
title_short Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives
title_sort biocatalytic decarboxylative michael addition for synthesis of 1,4-benzoxazinone derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9325775/
https://www.ncbi.nlm.nih.gov/pubmed/35882869
http://dx.doi.org/10.1038/s41598-022-16291-3
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