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 |
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| container_issue | 7 |
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| container_title | European journal of organic chemistry |
| container_volume | 2004 |
| creator | Busqué, Felix de March, Pedro Figueredo, Marta Font, Josep González, Lluïsa |
| description | 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) |
| doi_str_mv | 10.1002/ejoc.200300693 |
| format | Article |
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| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Furanones Lactones Michael addition Nucleophiles Sulfur |
| title | A Study of the Conjugate Addition of Thionucleophiles to 2(5H)-Furanones |
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