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Title

Enantioselective Organocatalytic Oxidation of Functionalized Sterically Hindered Disulfides

AuthorsKhiar el Wahabi, Noureddine ; Mallouk, Siham ; Valdivia, Victoria ; Bougrin, Khalid; Soufiaoui, Mohammed; Fernández Fernández, Inmaculada
KeywordsSulfoxides
Carbohydrates
Asymmetric catalysis
Diooxiranes
Hydroxylic
Enantioselectivity
Oxidation
Issue Date7-Mar-2007
PublisherAmerican Chemical Society
CitationOrganic Letters 9(7): 1255-1258 (2007)
AbstractThe first study on enantioselective oxidation of functionalized sterically hindered disulfides is reported. This study shows that the Shi organocatalytic system using carbohydrate-derived ketone with oxone is superior to the Ellman-Bolm vanadium catalyst in terms of chemical yield and enantioselectivity. Whereas the latter system afforded mostly racemic thiosulfinates in low to moderate yields, the former one afforded thiosulfinates with up to 96% ee.
Description4 páginas, 1 figura, 2 tablas, 2 esquemas.
Publisher version (URL)http://dx.doi.org/10.1021/ol070056z
URIhttp://hdl.handle.net/10261/37641
DOI10.1021/ol070056z
ISSN1523-7060
Appears in Collections:(IIQ) Artículos
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