Planar-Chiral Flavinium Salts ? Prospective Catalysts for Enantioselective Sulfoxidations

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F10%3A00023325" target="_blank" >RIV/60461373:22310/10:00023325 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Result language
angličtina
Original language name
Planar-Chiral Flavinium Salts ? Prospective Catalysts for Enantioselective Sulfoxidations
Original language description
A novel planar-chiral flavinium salt, 3-benzyl-5-ethyl-10-(8-phenyl-naphtalen-1-yl)isoalloxazinium perchlorate (2b), possessing a phenyl cap covering one site of the isoalloxazinium skeleton plane, was prepared as a potential catalyst of enantioselectiveH2O2 oxidations of sulfides. The rate of H2O2 oxidation of sulfides in the presence of racemic 2b is comparable with that of the reaction catalyzed by 5-ethyl-3,10-dimethylisoalloxazinium perchlorate, thus indicating that the bulky shielding substituentdoes not influence the catalytic activity of the flavinium unit. The turnover frequency of thioanisole oxidation with hydrogen peroxide for 2b is 870 h-1. Enantiomerically pure salts (+)-2b and (-)-2b were prepared from pure enantiomers (+)-3b and (-)-3b of 3-benzyl-10-(8-phenylnaphtalen-1-yl)isoalloxazin (3b) that are available by means of HPLC separation of racemic 3b on a chiral stationary phase. Enantiomerically pure salts (+)-2b and (-)-2b catalyze H2O2 oxidation of para-substitute
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
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Project
<a href="/en/project/GA203%2F07%2F1246" target="_blank" >GA203/07/1246: Chiral flavinium salts as organocatalysts for enantioselective sulfoxidations and N-oxidations</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2010
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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