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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/60461373:22310/13:43896601 RIV/60461373:22810/13:43896601

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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

Název v anglickém jazyce

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

Popis výsledku anglicky

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

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GAP208%2F11%2F0105" target="_blank" >GAP208/11/0105: Rozšíření metod vibrační optické aktivity pro oblast biomolekul</a><br>

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Svazek periodika

Neuveden

Číslo periodika v rámci svazku

34

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

15

Strana od-do

7724-7738

Kód UT WoS článku

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EID výsledku v databázi Scopus

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