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Updated: Sep 3, 2025

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Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives
Hossein Bavandi1, Mansour Shahedi1, Zohreh Habibi2
1Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C., Tehran, Iran.
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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