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DOI: 10.1055/a-2655-5237
TosMIC as a Powerful Reagent for Site-Selective α-Formamidomethylation of α-Enolic Dithioesters
Autoren
Gefördert durch: University Grants Commission (UGC)
Gefördert durch: the Anusandhan National Research Foundation, ANRF CRG/2023/000021
Gefördert durch: JC JCB/2020/000023
Funding Information We gratefully acknowledge the financial support from the Anusandhan National Research Foundation, ANRF (CRG/2023/000021); the IoE Incentive grant, BHU (Scheme No. 6031); and the JC Bose National Fellowship (JCB/2020/000023), New Delhi.
Dedication
Dedicated to Prof. H. Ila on her 80th birthday.
Abstract
Herein, we describe a metal-free facile method for the direct synthesis of α-formamidoalkyl-β-ketodithioesters by employing easily accessible α-enolic dithioesters (EDTEs) and p-tosylmethyl isocyanide (TosMIC) via base-mediated cross-detosylative C–C coupling under an open atmosphere. This protocol is mild, operationally simple, highly efficient, and easy to get highly functionalized products in good-to-high yields. A simple mechanism involving Cs2CO3 that promotes highly selective nucleophilic attack of the α-carbon of EDTE to TosMIC followed by hydrolysis is proposed. This efficient approach opens up a new avenue for exploring the synthesis of multifunctional molecules. The carbonyl, dithioester, and amide groups of the products offer a platform for late-stage modification, which could rapidly enrich the structural diversity of the products.
Publikationsverlauf
Eingereicht: 31. Mai 2025
Angenommen nach Revision: 15. Juli 2025
Accepted Manuscript online:
15. Juli 2025
Artikel online veröffentlicht:
20. August 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
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