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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 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.

SUBMITTER: Bavandi H

PROVIDER: S-EPMC9325775 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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

Bavandi Hossein H Shahedi Mansour M Habibi Zohreh Z Yousefi Maryam M Brask Jesper J Mohammadi Mehdi M

Scientific reports 20220726 1

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 ...[more]

PMID: 35882869

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