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.
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Yeom et al. (2008) studied this question.
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