ChemInform Abstract: The Copper Mediated Barbier Reactions of α,β‐Unsaturated Ketones: Regioselective Conjugate and 1,2‐Addition.

Abstract

The Copper Mediated Barbier Reactions of α,β-Unsaturated Ketones: Regioselective Conjugate and 1,2-Addition.-The one-pot reaction of isophorone (I) and other α,β-unsaturated ketones such as (V) and (VII) with alkyl and aryl halides (II) in the presence of magnesium and copper salts (Barbier conditions) leads to the regiospecific formation of 1,4-addition products. Contrary, Li-mediated reaction of model compound (I) with halides (II) results in regioselective 1,2-addition [→(IV)]. -(COSTELLO, DECLAN P.; GERAGHTY, NIALL W. A.; Synth. Commun. 29 (1999) 18, 3083-3096; Chem. Dep., Nat. Univ. Ire., Galway, Ire.; EN)