Biocatalytic Friedel-Crafts Acylation and Fries Reaction

Nina G. Schmidt, Tea Pavkov-Keller, Nina Richter, Birgit Wiltschi, Karl Gruber*, Wolfgang Kroutil*

*Korrespondierende/r Autor/in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikel

Abstract

The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C−C bond formation methods.
Originalspracheenglisch
Seiten (von - bis)7615-7619
FachzeitschriftAngewandte Chemie / International Edition
Jahrgang56
Ausgabenummer26
DOIs
PublikationsstatusVeröffentlicht - 23 Mai 2017

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