1603833-13-1Relevant articles and documents
Synthesis of Monothiomalonates – Versatile Thioester Enolate Equivalents for C–C Bond Formations
Engl, Oliver D.,Saadi, Jakub,Cosimi, Elena,Wennemers, Helma
, (2017/12/01)
Monothiomalonates (MTMs) are surrogates of thioester enolates that allow for stereoselective C–C bond formations under mild conditions and thereby afford access to synthetically versatile thioester derivatives. Here we present a straightforward synthetic route to MTMs that proceeds through nucleophilic ring-opening of Meldrum's acid derivatives followed by O-alkylation of the resulting malonic acid half thioesters with alkyl triflates or acetimidates as electrophiles. The method affords MTMs in overall yields of 34?–?92% and allows for variations of the oxo- and thioester moieties as well as the substituent at the C(α) position.