Highly enantioselective catalytic phenylation of ketones with a constrained geometry titanium catalyst.

[reaction: see text] The catalytic asymmetric addition of phenyl groups from diphenylzinc to ketones is reported. The catalyst, generated from a dihydroxy bis(sulfonamide) ligand and titanium tetraisopropoxide, gives good to excellent enantioselectivities with a range of substrates.

[1]  P. Walsh,et al.  Asymmetric addition of alkylzinc reagents to cyclic alpha,beta-unsaturated ketones and a tandem enantioselective addition/diastereoselective epoxidation with dioxygen. , 2003, Journal of the American Chemical Society.

[2]  M. Yus,et al.  Highly enantioselective arylation of ketones , 2003 .

[3]  C. Bolm,et al.  Phenyl versus ethyl transfer in the addition of organozinc reagents to aldehydes: a theoretical study. , 2003, Angewandte Chemie.

[4]  K. Koga,et al.  Camphorqu1none and camphorquinone monoxime , 2003 .

[5]  James D White,et al.  (2S)‐(−)‐3‐exo‐(Dimethylamino)Isoborneol [(2S)‐(−)‐DAIB] , 2003 .

[6]  M. Yus,et al.  Highly enantioselective addition of dialkylzinc reagents to ketones promoted by titanium tetraisopropoxide , 2002 .

[7]  D. Ha,et al.  Enantioselective additions of diethylzinc and diphenylzinc to aldehydes using 2-dialkyl-aminomethyl-2'-hydroxy- 1,1'-binaphthyls. , 2002, Organic letters.

[8]  P. Walsh,et al.  A practical catalytic asymmetric addition of alkyl groups to ketones. , 2002, Journal of the American Chemical Society.

[9]  C. Bolm,et al.  Catalyzed Asymmetric Arylation Reactions. , 2001, Angewandte Chemie.

[10]  L. Pu,et al.  Catalytic asymmetric organozinc additions to carbonyl compounds. , 2001, Chemical reviews.

[11]  Gang Zhao,et al.  Enantioselective additions of diphenylzinc to aldehydes using chiral pyrrolidinylmethanol derivatives as catalysts , 2001 .

[12]  Muñiz,et al.  Asymmetric, Catalytic Phenyl Transfer to Aldehydes: Enantioselective Synthesis of Diarylmethanols We are grateful to the Fonds der Chemischen Industrie and to the Deutsche Forschungsgemeinschaft (DFG) within the Collaborative Research Center (SFB) 380 "Asymmetric Synthesis by Chemical and Biological , 2000, Angewandte Chemie.

[13]  L. Pu,et al.  New and improved ligands for highly enantioselective catalytic diphenylzinc additions to aryl aldehydes , 2000 .

[14]  M. Yus,et al.  First enantioselective addition of diethylzinc and dimethylzinc to prostereogenic ketones catalysed by camphorsulfonamide-titanium alkoxide derivatives , 1998 .

[15]  M. Yus,et al.  FIRST ENANTIOSELECTIVE ADDITION OF DIALKYLZINC TO KETONES PROMOTED BY TITANIUM(IV) DERIVATIVES , 1998 .

[16]  P. Dosa,et al.  Catalytic Asymmetric Addition of ZnPh2 to Ketones: Enantioselective Formation of Quaternary Stereocenters , 1998 .

[17]  P. Walsh,et al.  Synthesis of new chiral tetradentate sulfonamide based ligands , 1997 .

[18]  Xumu Zhang,et al.  Enantioselective addition of diethylzinc to benzaldehyde catalyzed by chiral titanate complexes with helical ligands , 1997 .

[19]  P. Dosa,et al.  Planar-Chiral Heterocycles as Ligands in Metal-Catalyzed Processes: Enantioselective Addition of Organozinc Reagents to Aldehydes. , 1997, The Journal of organic chemistry.

[20]  K. Soai,et al.  Enantioselective Addition of Organozinc Reagents to Aldehydes , 1992 .

[21]  R. Noyori,et al.  Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes. , 1986, Journal of the American Chemical Society.