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Chlorine Atom Transfer Radical 6‐ exo Cyclizations of Carbamoyldichloroacetate‐Tethered Alkenes, Enol Acetates and α,β‐Unsaturated Nitriles Leading to Morphans
Author(s) -
Diaba Faïza,
MartínezLaporta Agustín,
Bonjoch Josep
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301590
Subject(s) - chemistry , cyclopropane , enol , radical cyclization , ring (chemistry) , electron transfer , medicinal chemistry , chlorine atom , double bond , radical ion , photochemistry , atom (system on chip) , stereochemistry , organic chemistry , catalysis , ion , computer science , embedded system
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.