Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers.
The copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted cyclic enones affords enantioenriched all-carbon quaternary centers with up to 96% ee. The chiral ligand is a diaminocarbene, directly generated in situ. The combination of Grignard reagent and diaminocarbene is unprecedented in conjugate addition, and the additon of the phenyl group, on such enones, cannot be done by other conjugate addition methods.
Martin
David
D
Département de Chimie Organique, Université de Genève, 30 quai Ernest Ansermet, CH-1211 Genève 4, Switzerland.
Kehrli
Stefan
S
d'Augustin
Magali
M
Clavier
Hervé
H
Mauduit
Marc
M
Alexakis
Alexandre
A
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D005609:Free Radicals; D007202:Indicators and Reagents; D007659:Ketones; D008024:Ligands; D009942:Organometallic Compounds; D003300:Copper