A Study of the Conjugate Addition of Thionucleophiles to 2(5H)-Furanones

A Study of the Conjugate Addition of Thionucleophiles to 2(5H)-Furanones

Several new 4‐thio‐4,5‐dihydro‐2(3H)‐furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5H)‐furanones. When 5‐methyl‐2(5H)‐furanone was used as the electrophilic substrate, the reaction was diastereoselective affording...

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Veröffentlicht in:European journal of organic chemistry 2004-04, Vol.2004 (7), p.1492-1499
Hauptverfasser: Busqué, Felix, de March, Pedro, Figueredo, Marta, Font, Josep, González, Lluïsa
Format: Artikel
Sprache:eng
Schlagworte:
Furanones
Lactones
Michael addition
Nucleophiles
Sulfur
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Zusammenfassung:Several new 4‐thio‐4,5‐dihydro‐2(3H)‐furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5H)‐furanones. When 5‐methyl‐2(5H)‐furanone was used as the electrophilic substrate, the reaction was diastereoselective affording exclusively the cis‐α,β‐disubstituted butanolides. Some adducts were selectively hydrolysed to deliver a free thiol functionality. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300693