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Alloxazine-cyclodextrin conjugates for organocatalytic enantioselective sulfoxidations

SYSNO ASEP	0367200
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Alloxazine-cyclodextrin conjugates for organocatalytic enantioselective sulfoxidations
Author(s)	Mojr, V. (CZ) Buděšínský, Miloš (UOCHB-X)_{RID, ORCID} Cibulka, R. (CZ) Kraus, Tomáš (UOCHB-X)_{RID, ORCID}
Number of authors	4
Source Title	Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520 Roč. 9, č. 21 (2011), s. 7318-7326
Number of pages	9 s.
Language	eng - English
Country	GB - United Kingdom
Keywords	cyclodextrins ; alloxazines ; sulfoxidations
Subject RIV	CC - Organic Chemistry
R&D Projects	GA203/07/1246 GA ČR - Czech Science Foundation (CSF)
	GA203/09/1919 GA ČR - Czech Science Foundation (CSF)
CEZ	AV0Z40550506 - UOCHB-X (2005-2011)
UT WOS	000295890100011
DOI	10.1039/c1ob05934c
Annotation	Four structurally different alloxazine–cyclodextrin conjugates were prepared and tested as catalysts for the enantioselective oxidation of prochiral sulfides to sulfoxides by hydrogen peroxide in aqueous solutions. Alpha-cyclodextrin conjugate having alloxazinium unit attached via a short linker proved to be a suitable catalyst for oxidations of n-alkyl methyl sulfides, displaying conversions up to 98% and enantioselectivities up to 77% ee. Beta-cyclodextrin conjugates were optimal catalysts for the oxidation of sulfides carrying bulkier substituents; e.g. tert-butyl methyl sulfide was oxidized with quantitative conversion and 91% ee. Low loadings (0.3–5 mol%) of the catalysts were used.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2012

Number of the records: 1