Pyrrolo[2,1-b]thiazole derivatives by asymmetric 1,3-dipolar reactions of thiazolium azomethine ylides to activated vinyl sulfoxides

The Journal of Organic Chemistry
José L García RuanoCristina Fajardo


1,3-Dipolar reactions of thiazolium azomethine ylides to enantiopure cyclic and acyclic vinyl sulfoxides provide an efficient access to polyfunctionalized pyrrolo[2,1-b][1,3]thiazoles in a highly regio- and stereoselective manner. Regioselectivity can be inverted by modifying the position of the sulfinyl group at the double bond of the sulfinylfuranones. The sulfoxide is the main controller of the endo selectivity of these processes as well as of the pi-facial selectivity in reactions of (Z)-3-p-tolylsulfinylacrylonitriles. In contrast, the pi-facial selectivity in reactions of 5-alkoxy-3-p-tolylsulfinyl furan-2(5H)-ones is mainly controlled by the configuration at C-5, affording the anti adducts with respect to the alkoxy group as the major or exclusive adducts.


Jul 11, 2000·Bioorganic & Medicinal Chemistry Letters·K R PrakashA P Kozikowski
Oct 24, 2001·The Journal of Organic Chemistry·J. L. García RuanoM. Martínez-Ripoll
Dec 20, 2003·The Journal of Organic Chemistry·José Luis García RuanoM Teresa Peromingo
Oct 22, 2005·The Journal of Organic Chemistry·José L García RuanoAmelia Tito
Aug 12, 2006·The Journal of Organic Chemistry·José L García RuanoAlberto Núñez
May 17, 2007·Journal of the American Chemical Society·William L ScottMartin J O'Donnell

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