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...
Published in: | Scientific Reports |
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Main Authors: | , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Nature Portfolio
2022
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Subjects: | |
Online Access: | https://doi.org/10.1038/s41598-022-16291-3 https://doaj.org/article/c3ecb44a8c2f4d7c8e760622b80aa245 |
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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