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Enzyme and photoredox sequential catalysis for the synthesis of 1,3-oxazine derivatives in one pot

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Abstract

A novel strategy combining visible-light and enzyme catalysis in one pot for the synthesis of 1,3-oxazine derivatives from α- or β-naphthols and ethyl N-aryl glycinates is described for the first time. Various 1,3-oxazine derivatives were prepared with yields of up to 69% under mild reaction conditions by a simple operation. This approach consists of sequential enzymatic hydrolysis and visible-light excited decarboxylation of ethyl N-aryl glycinates, oxidation of α-amino radicals, Mannich reaction, transimination and intramolecular cyclization. This work provides a novel alternative method for the synthesis of 1,3-oxazine derivatives.

Graphical abstract: Enzyme and photoredox sequential catalysis for the synthesis of 1,3-oxazine derivatives in one pot

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Publication details

The article was received on 26 Dec 2016, accepted on 27 Mar 2017 and first published on 28 Mar 2017


Article type: Paper
DOI: 10.1039/C6CY02682F
Citation: Catal. Sci. Technol., 2017, Advance Article
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    Enzyme and photoredox sequential catalysis for the synthesis of 1,3-oxazine derivatives in one pot

    G. Zhang, Y. Xiang, Z. Guan and Y. He, Catal. Sci. Technol., 2017, Advance Article , DOI: 10.1039/C6CY02682F

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