Enantioselective Cu-catalyzed conjugate addition of diethylzinc to acyclic aliphatic enones.
[reaction: see text] A new P-chiral phosphine bis(sulfonamide) ligand has been developed that allows the Cu-catalyzed enantioselective conjugate addition of Et(2)Zn to acyclic aliphatic enones. The reactions proceed with excellent levels of enantioselectivity (90-95% ee) with a range of enone substrates, involve the use of only 1.2 equiv of Et(2)Zn, and give best results at ambient temperature.
Duncan
Andrew P
AP
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Leighton
James L
JL
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis*; D013696:Temperature
D007659:Ketones; D008024:Ligands; D009942:Organometallic Compounds; D010720:Phosphines; D013449:Sulfonamides; D003300:Copper; C044646:phosphine; C454811:diethylzinc