Synthesis of Trimethyl α-Keto Trithioorthoesters and Dimethyl α-Keto Dithioacetals by Reaction of Esters with Tris(methylthio)methyllithium

Article abstract of DOI:10.1021/jo00124a009

A complete study has been made of the reaction of tris(methylthio)methyllithium with aromatic, heteroaromatic, and aliphatic esters.It is a one-pot reaction that despite its complexity, and depending on the reagent ratios, the reaction conditions, and the possible use of additional reagents (N-(methylthio)phthalimide or BuLi), can supply easily, in excellent and reproducible yields, the trimethyl α-keto trithioorthoesters 3 or, alternatively, the dimethyl α-keto dithioacetals 4.The reaction mechanism has been elucidated.