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

摘要

The Cu~1-mediate d 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~1, Pd, or Zn.