Cu(II)-catalyzed acylation by thiol esters under neutral conditions: tandem acylation-wittig reaction leading to a one-pot synthesis of butenolides.
The first catalytic acylation of alcohols with a thiol ester present in Wittig reagents under neutral conditions catalyzed by the Cu(II) salt through a push-pull mechanism is reported. Furthermore, a new methodology for the one-pot lactonization of acyloins by a copper catalyst is developed. The synthetic utility of this method for the synthesis of natural products is shown.
Matsuo
Kazumasa
K
Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, Kasuga-koen, Kasuga 816-8580, Japan.
Shindo
Mitsuru
M
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000215:Acylation; D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D004952:Esters; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000438:Alcohols; D004952:Esters; D013438:Sulfhydryl Compounds; D003300:Copper; C004511:butenolide; D015107:4-Butyrolactone