Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis
5 years ago

α-Keto Thioesters as Building Blocks for Accessing γ-Hydroxybutenolides and Oxazoles

α-Keto Thioesters as Building Blocks for Accessing γ-Hydroxybutenolides and Oxazoles
Indrajit Das, Kanchan Mal
α-Keto thioesters, with two electrophilic carbon centres, have been found to react differently with β-keto esters and isocyanoacetates. They undergo base induced Knoevenagel-type condensation on the keto carbonyl group with β-keto esters, followed by intramolecular cyclization and water addition leads to highly substituted γ-hydroxybutenolides. On the other hand, substituted oxazole derivatives have been obtained using isocyanoacetates via nucleophilic displacement on the thioester carbonyl followed by intramolecular cyclization. Further functionalization of the γ-hydroxybutenolides is also demonstrated via a BF3.OEt2-mediated cation-driven nucleophilic addition of terminal alkynes to access multiply substituted butenolides.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700329

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