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

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About: Planar chiral flavinium salts: Synthesis and evaluation of the effect of substituents on the catalytic efficiency in enantioselective sulfoxidation reactions Goto Sponge NotDistinct Permalink

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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, or substitution 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 methyl sulfide. 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, or substitution 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 methyl sulfide. (en)
Title	Planar chiral flavinium salts: Synthesis and evaluation of the effect of substituents on the catalytic efficiency in enantioselective sulfoxidation reactions Planar chiral flavinium salts: Synthesis and evaluation of the effect of substituents on the catalytic efficiency in enantioselective sulfoxidation reactions (en)
skos:prefLabel	Planar chiral flavinium salts: Synthesis and evaluation of the effect of substituents on the catalytic efficiency in enantioselective sulfoxidation reactions Planar chiral flavinium salts: Synthesis and evaluation of the effect of substituents on the catalytic efficiency in enantioselective sulfoxidation reactions (en)
skos:notation	RIV/60461373:22310/13:43896601!RIV14-MSM-22310___
http://linked.open...avai/predkladatel	Fakulta chemické technologie
http://linked.open...avai/riv/aktivita	P S
http://linked.open...avai/riv/aktivity	P(GAP208/11/0105), S
http://linked.open...iv/cisloPeriodika	34
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Hodačová, Jana Cibulka, Radek Eigner, Václav Jurok, Radek
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta chemické technologie
http://linked.open...dnocenehoVysledku	96344
http://linked.open...ai/riv/idVysledku	RIV/60461373:22310/13:43896601
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	organocatalysis; asymmetric oxidation; sulfoxidation; flavins (en)
http://linked.open.../riv/klicoveSlovo	asymmetric oxidation sulfoxidation flavins organocatalysis
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[B6DD0608FBBB]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	4 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...vavai/riv/projekt	Expanding the Optical Activity Method to the Realm of Biomolecules
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	Neuveden
http://linked.open...iv/tvurceVysledku	Cibulka, Radek Hodačová, Jana Dvořáková, Hana Eigner, Václav Setnička, Vladimír Jurok, Radek
issn	1434-193X
number of pages	15 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201300847
http://localhost/t...ganizacniJednotka	22310

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