We demonstrate that ?-amino-1-iodo-1-alkenes undergo cyclization/dimerization reactions. The reaction selectively generates bis-pyrrolidines with a meso configuration and can be used to make 1,2-bis-(2-piperidinyl)ethanes like those found in the alkaloid hyalbidone. In the presence of norbornadiene the reaction generates cyclopropanes. Several mechanisms are consistent with the observed patterns of reactivity.

Dimerization of terminal 1-iodo-1-alkenes with pendant nucleophiles

245th National Meeting (2013)

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