Efficient One-Pot Synthesis of α-Alkylated β-Ketothioesters from H2SO4- Catalyzed Tandem Alkylation/Hydrolysis Reaction of Acyclic α-Oxo Ketene Dithioacetals with Alcohols

Title:Efficient One-Pot Synthesis of α-Alkylated β-Ketothioesters from H2SO4- Catalyzed Tandem Alkylation/Hydrolysis Reaction of Acyclic α-Oxo Ketene Dithioacetals with Alcohols

Volume: 15 Issue: 11

Author(s): Diangang Bai, Haifeng Yu*, Quanping Diao and Tiechun Li

Affiliation:

• School of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 114007,China

Keywords: Thioester, tandem reaction, sulfuric acid, ketene dithioacetal, alcohol, alkylation, hydrolysis.

Abstract: In the paper, we wish to report an efficient one-pot synthesis of α-alkylated β-ketothioesters based on H2SO4-catalyzed tandem alkylation/hydrolysis reaction between acyclic α-oxo ketene dithioacetals and alcohols. It was shown that the tandem reaction could efficiently occur in the presence of 5 mol% H2SO4 at room temperature in CH3CN, affording the desired α-alkylated β-ketothioesters in excellent yields. The use of very small amounts of catalyst, good generality, low cost of the reagents, excellent yield and mild reaction conditions outline the notable features of the reaction.

Cite this article as:

Bai Diangang , Yu Haifeng *, Diao Quanping and Li Tiechun , Efficient One-Pot Synthesis of α-Alkylated β-Ketothioesters from H2SO4- Catalyzed Tandem Alkylation/Hydrolysis Reaction of Acyclic α-Oxo Ketene Dithioacetals with Alcohols, Letters in Organic Chemistry 2018; 15 (11) . https://dx.doi.org/10.2174/1570178615666180326161157