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Gold-Catalyzed Waste-Free Generation and Reaction of Azomethine Ylides: Internal Redox/Dipolar Cycloaddition Cascade


  • This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD, Basic Research Promotion Fund, KRF-2007-313-C00408). We gratefully thank Prof. Shim Sung Lee (GNU) for X-ray crystallographic analysis.


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High-octane synthesis: Azomethine ylides can be generated from an internal redox reaction of a nitrone-tethered alkyne under electrophilic metal catalysis (see scheme; M=metal). This novel and atom-economical generation of an azomethine ylide does not involve potentially explosive diazo derivatives. The azomethine ylide can participate in a dipolar cycloaddition cascade to provide an azabicyclo[3.2.1]octane.