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Vinylation of Unprotected Phenols Using a Biocatalytic System

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논문

Vinylation of Unprotected Phenols Using a Biocatalytic System

학술지

Angewandte Chemie

저자명

Busto, Eduardo; Simon, Robert C.; Kroutil, Wolfgang

초록

<P><B>Abstract</B></P><P>Readily available substituted phenols were coupled with pyruvate in buffer solution under atmospheric conditions to afford the corresponding para&#8208;vinylphenol derivatives while releasing only one molecule of CO<SUB>2</SUB> and water as the by&#8208;products. This transformation was achieved by designing a biocatalytic system that combines three biocatalytic steps, namely the C&#63743;C coupling of phenol and pyruvate in the presence of ammonia, which leads to the corresponding tyrosine derivative, followed by deamination and decarboxylation. The biocatalytic transformation proceeded with high regioselectivity and afforded exclusively the desired <I>para</I> products. This method thus represents an environmentally friendly approach for the direct vinylation of readily available 2&#8208;, 3&#8208;, or 2,3&#8208;disubstituted phenols on preparative scale (0.5&#8197;mmol) that provides vinylphenols in high yields (65&ndash;83&thinsp;%).</P>

발행연도

2015

발행기관

WILEY&#x2010;VCH Verlag

ISSN

0044-8249

ISSN

1521-3757

127

37

페이지

pp.11049-11052

주제어

Biotransformationen; C&#x2010; C&#x2010; Bindungskn&uuml; pfung; Enzymkatalyse; Kaskadenreaktionen; Vinylierungen;

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1 2023-12-11

논문; 2015-07-29

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