Chlorine Atom Transfer Radical 6-exo Cyclizations of Carbamoyldichloroacetate- Tethered Alkenes, Enol Acetates and α,β- Unsaturated Nitriles Leading to Morphans

The Cu-I-mediated atom transfer radical cyclization of amino-tethered dichloromalonamides and electron-rich, electron-poor, and nonactivated double bonds is a useful methodology for the synthesis of 2-azabicyclo[3.3.1]nonanes. A study of the reaction conditions and the scope of the process is reported. Cyclopropane ring formation was observed from the resulting 1,3-dichlorides in some morphan substrates using either Cu-I, Pd, or Zn.