Direct β-Activation of Saturated Aldehydes to Formal Michael Acceptors through Oxidative NHC Catalysis†
Junming Mo
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) http://www.ntu.edu.sg/home/robinchi
Search for more papers by this authorLiang Shen
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) http://www.ntu.edu.sg/home/robinchi
Search for more papers by this authorCorresponding Author
Prof. Dr. Yonggui Robin Chi
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) http://www.ntu.edu.sg/home/robinchi
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) http://www.ntu.edu.sg/home/robinchiSearch for more papers by this authorJunming Mo
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) http://www.ntu.edu.sg/home/robinchi
Search for more papers by this authorLiang Shen
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) http://www.ntu.edu.sg/home/robinchi
Search for more papers by this authorCorresponding Author
Prof. Dr. Yonggui Robin Chi
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) http://www.ntu.edu.sg/home/robinchi
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) http://www.ntu.edu.sg/home/robinchiSearch for more papers by this authorWe 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.
Graphical Abstract
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.
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