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Acid-Mediated Highly Regioselective Oxidation of Substituted Furans: A Simple and Direct Entry to Substituted Butenolides

AuthorsCeñal, Juan P.; Carreras, Carlos R.; Tonn, Carlos E.; Padrón, Juan I. ; Ramírez, Miguel A.; Díaz Díaz, David ; García-Tellado, Fernando ; Martín, Víctor S.
Substituted butenolides
Issue DateJun-2005
CitationSynlett 2005(10): 1575-1578 (2005)
AbstractThe scope and limitations of an expeditious synthesis of substituted butenolides from 3-substituted or 3,4-disubstituted furans is described. The entire process embodies a controlled oxidation of the furan core to a 2,5-dialkoxy-dihydrofuran intermediate and a regioselective acid-catalyzed hydrolysis to the butenolide ­derivative. 3-Substituted furans yield exclusively 2-substituted butenolides. Calculations studies provide substantiation of a proposed mechanism.
Description4 pages, 2 tables, 3 schemes.
Publisher version (URL)http://dx.doi.org/10.1055/s-2005-869865
Appears in Collections:(IPNA) Artículos
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