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

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

Journal Name: Letters in Organic Chemistry

Volume 15 , Issue 11 , 2018

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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.

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

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Article Details

VOLUME: 15
ISSUE: 11
Year: 2018
Page: [905 - 908]
Pages: 4
DOI: 10.2174/1570178615666180326161157
Price: $65

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