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Artificial Flavin Systems for Chemoselective and Stereoselective Oxidations (Eur. J. Org. Chem. 5/2015)
Author(s) -
Cibulka Radek
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201590009
Subject(s) - chemistry , flavin group , chemoselectivity , moiety , stereoselectivity , homolysis , divergent synthesis , monooxygenase , hydrogen peroxide , cofactor , combinatorial chemistry , stereochemistry , flavoprotein , catalysis , organic chemistry , enzyme , cytochrome p450 , radical
The cover picture shows 5‐alkylflavin hydroperoxide, which is the active species in oxygenations catalysed by flavinium salts. Binding to the flavin moiety significantly enhances the reactivity of oxygen and hydrogen peroxide allowing various types of oxygenations to proceed under mild conditions with high chemoselectivity. Examples include sulfoxidations, N‐oxidations, Baeyer–Villiger and Dakin oxidations, oxidations of aldehydes to carboxylic acids, or the insertion of oxygen into the rhenium–methyl bond. Artificial flavin‐based catalytic systems have been inspired by flavin‐dependent monooxygenases, which utilize hydroperoxide formed from a flavin cofactor as shown in the mirror. Details are presented in the Microreview by R. Cibulka on 915 ff .