TY - JOUR
T1 - A study of the conjugate addition of thionucleophiles to 2(5H)-furanones
AU - Busqué, Felix
AU - De March, Pedro
AU - Figueredo, Marta
AU - Font, Josep
AU - González, Lluïsa
PY - 2004/3/26
Y1 - 2004/3/26
N2 - 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.
AB - 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.
KW - Furanones
KW - Lactones
KW - Michael addition
KW - Nucleophiles
KW - Sulfur
U2 - 10.1002/ejoc.200300693
DO - 10.1002/ejoc.200300693
M3 - Article
SN - 1434-193X
SP - 1492
EP - 1499
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 7
ER -