Planar chiral flavinium salts: Synthesis and evaluation of the effect of substituents on the catalytic efficiency in enantioselective sulfoxidation reactions

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F13%3A43896601" target="_blank" >RIV/60461373:22340/13:43896601 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/13:43896601 RIV/60461373:22810/13:43896601
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201300847" target="_blank" >http://dx.doi.org/10.1002/ejoc.201300847</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201300847" target="_blank" >10.1002/ejoc.201300847</a>

Result language
angličtina
Original language name
Planar chiral flavinium salts: Synthesis and evaluation of the effect of substituents on the catalytic efficiency in enantioselective sulfoxidation reactions
Original language description
A series of substituted planar chiral flavinium salts with phenyl cap were prepared as potential catalysts for enantioselective sulfoxidations with hydrogen peroxide, using an approach based on the synthesis of arylaminouracils and their condensation with substituted nitrosobenzenes. The effect of substituents at various positions on the ability of the catalyst to promote enantioselective sulfoxidations was investigated. Introduction of the tyrosine group into the side chain of the flavinium species, orsubstitution of nitrogen N(3) of the flavin unit by ortho-isopropylphenyl group has a remarkably positive effect on the enantioselectivity of sulfoxidations of aromatic and aliphatic substrates, respectively. On the other hand, substitution of the phenyl cap substantially decreases the efficiency of the catalyst. In summary, optimisation of the structure of planar chiral flavinium catalysts led to enantioselectivities up to 61% ee for aromatic sulfides and up to 65% ee for tert-butyl me
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—

Project
<a href="/en/project/GAP208%2F11%2F0105" target="_blank" >GAP208/11/0105: Expanding the Optical Activity Method to the Realm of Biomolecules</a><br>
Continuities
S - Specificky vyzkum na vysokych skolach

Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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