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.
|Journal||European Journal of Organic Chemistry|
|Publication status||Published - 26 Mar 2004|
- Michael addition