1, 4-Addition of Diorganozincs to. ALPHA.,. BETA.-Unsaturated Ketones Catalyzed by a Copper (I)-Sulfonamide Combined System.

M Kitamura, T Miki, K Nakano, R Noyori

Index: Kitamura, Masato; Miki, Takashi; Nakano, Keiji; Noyori, Ryoji Bulletin of the Chemical Society of Japan, 2000 , vol. 73, # 4 p. 999 - 1014

Full Text: HTML

Citation Number: 76

Abstract

A mixture of CuCN and N-benzylbenzenesulfonamide catalyzes the 1, 4-addition of dialkylzincs or diarylzincs (Cu: Zn= 1: 200 to 1: 10000) to α, β-unsaturated ketones to give, after aqueous workup, the corresponding β-substituted ketones in nearly quantitative yields. A range of cyclic enones having s-cis or s-trans geometries as well as conformationally flexible acyclic enones are usable as substrates. The ethyl group migrates more readily ...

Related Articles:

A New Catalytic Activity of Antimony (III) Chloride in Palladium (0)-Catalyzed Conjugate Addition of Aromatics to. alpha.,. beta.-Unsaturated Ketones and Aldehydes …

[Journal of Organic Chemistry, , vol. 60, # 4 p. 883 - 888]

Rhodium-catalyzed conjugate addition of aryl-and alkenyl-stannanes to α, β-unsaturated carbonyl compounds

[Oi, Shuichi; Moro, Mitsutoshi; Ito, Hisanori; Honma, Yoshio; Miyano, Sotaro; Inoue, Yoshio Tetrahedron, 2002 , vol. 58, # 1 p. 91 - 97]

A New Catalytic Activity of Antimony (III) Chloride in Palladium (0)-Catalyzed Conjugate Addition of Aromatics to. alpha.,. beta.-Unsaturated Ketones and Aldehydes …

[Cho, Chan Sik; Motofusa, Shin-ichi; Ohe, Kouichi; Uemura, Sakae; Shim, Sang Chul Journal of Organic Chemistry, 1995 , vol. 60, # 4 p. 883 - 888]

Phosphine–olefin ligands: a facile dehydrogenative route to catalytically active rhodium complexes

[Douglas, Thomas M.; Notre, Jerome Le; Brayshaw, Simon K.; Frost, Christopher G.; Weller, Andrew S. Chemical Communications, 2006 , # 32 p. 3408 - 3410]

Ni-catalyzed asymmetric addition of Grignard reagents to unsaturated cyclic acetals. The influence of added phosphine on enantioselectivity

[Gomez-Bengoa; Heron; Didiuk; Luchaco; Hoveyda Journal of the American Chemical Society, 1998 , vol. 120, # 30 p. 7649 - 7650]

More Articles...