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Direct β-Activation of Saturated Aldehydes to Formal Michael Acceptors through Oxidative NHC Catalysis


  • We thank the Singapore National Research Foundation (NRF), the Singapore Economic Development Board (EDB), and GlaxoSmithKline (GSK) for generous financial support, and Dr. Y. Li and Dr. R. Ganguly at the Nanyang Technological University (NTU) for X-ray structures. NHC=N-heterocyclic carbene.


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Without detours: Oxidative catalysis mediated by N-heterocyclic carbenes (NHCs) enables the direct β-carbon functionalization of saturated aldehydes (see scheme). The reaction proceeds through two sequential oxidative steps to generate α,β-unsaturated triazolium ester equivalents as formal Michael acceptors, which react with 1,3-diketones and β-ketone esters in an enantioselective manner.