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DMAP-catalysed sulfinylation of diacetone-D-glucose: Improved method for the synthesis of enantiopure tert-butyl sulfoxides and tert-butanesulfinamides

AutorChelouan, Ahmed; Recio, Rocío; Alcudia, Ana; Khiar el Wahabi, Noureddine ; Fernández Fernández, Inmaculada
Palabras claveSulfoxides
Steric hindrance
Chiral auxiliaries
Sulfur
Asymmetric synthesis
Fecha de publicación2014
EditorWiley-VCH
CitaciónEuropean Journal of Organic Chemistry 2014: 6935- 6944 (2014)
Resumen© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. An improved method for the tert-butanesulfinylation of diacetone glucose with tert-butanesulfinyl chloride is reported. The method is based on a beneficial effect of catalytic DMAP, which enhances both the rate of the reaction and the enantioselectivity of the process to give (RS)-diastereomer 2RS with a 94%de and in quantitative yield. (RS)-DAG sulfinate ester 2RS is an excellent intermediate for the synthesis of enantiopure tert-butyl sulfoxides. Grignard agents and organolithium reagents can displace smoothly the diacetone glucose moiety to give synthetically relevant enantiopure sulfoxides, including highly functionalized derivatives, in high yields and with high enantioselectivities. (RS)-DAG sulfinate ester 2RS is also an excellent N-sulfinylating agent; simple addition of LiHMDS (lithium hexamethyldisilazide) in THF gives (SS)-tert-butanesulfinamide, and N-tert-butanesulfinylimines are then formed in a two-step one-pot manner. N-Alkylated tert-butanesulfinamides are formed by the condensation of 2RS with lithium amides.
URIhttp://hdl.handle.net/10261/108752
DOI10.1002/ejoc.201402673
Identificadoresdoi: 10.1002/ejoc.201402673
issn: 1099-0690
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