Catalytic asymmetric addition of diphenylzinc to cyclic alpha,beta-unsaturated ketones.
We have examined the use of our bis(sulfonamide) diol ligand (1) in the asymmetric addition of phenyl groups to cyclic alpha,beta-unsaturated ketones. Good to excellent enantioselectivities have been obtained with cyclic enones bearing alkyl substituents in the 2 position (71-97% enantiomeric excess). Furthermore, excellent enantioselectivities have been observed in the asymmetric phenylation of cyclic enones with 2-iodo and 2-bromo substituents. The results of this study broaden the scope of the asymmetric additions to ketones promoted by the titanium catalyst derived from ligand 1.
Li
Hongmei
H
P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323, USA.
García
Celina
C
Walsh
Patrick J
PJ
D000438:Alcohols / Q000138:chemical synthesis*; D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000438:Alcohols; D001713:Biphenyl Compounds; D006842:Hydrocarbons, Brominated; D006847:Hydrocarbons, Iodinated; D007659:Ketones; D009942:Organometallic Compounds; D015032:Zinc