A formal [4+2] cycloaddition between incipient N-amidinyliminium ions and several electron-rich heterocycles, mediated by an N-fluoropyridinium salt promoter, gives rise to previously unknown polycyclic guanidine containing architectures. Three contiguous stereocenters are formed with good diastereocontrol in the transformation, including one all-carbon quarternary center. 

Formal [4+2] cycloadditions between incipient <i>N</i>-amidinyliminium ions and electron-rich heterocycles: Accessing unknown polycyclic guanidine containing alkaloid architectures

246th National Meeting (2013)

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Formal [4+2] cycloadditions between incipient N-amidinyliminium ions and electron-rich heterocycles: Accessing unknown polycyclic guanidine containing alkaloid architectures