Rhodium(I)-, iridium(I)-, and ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using diferrocenyl dichalcogenides as chiral ligands
作者： Yoshiaki Nishibayashi , Jai Deo Singh , Yasuyoshi Arikawa , Sakae Uemura , Masanobu Hidai
DOI: 10.1016/S0022-328X(96)06681-8
关键词:
摘要: Abstract [R,S;R,S]-Bis[2-[1-(dimethylamino)ethyl]ferrocenyl] dichalcogenides. (R,S)-{[EC5H3CHMe(NMe2)]Fe(C5H5)}2 (ES, Se, Te), act as chiral ligands for Rh(I)-catalyzed asymmetric transfer hydrogenation of alkyl aryl ketones using a diphenylsilane/methanol system to give the corresponding alcohols in fair good yields with moderate enantiomeric excess (22–95% ee). The hydrogen from methanol resultant alcohol is confirmed by experiment deuterated (MeOD), and new catalytic containing Rh-hydride species proposed. In well-known 2-propanol/base system, stereoselection not satisfactory Rh(I)-, h(I)- Ru(II)-catalyzed reactions these ligands.
elsevier.com
sci-hub.se 参考文章(34)
Jing-Xing Gao, Takao Ikariya, Ryoji Noyori, A Ruthenium(II) Complex with a C2-Symmetric Diphosphine/Diamine Tetradentate Ligand for Asymmetric Transfer Hydrogenation of Aromatic Ketones† Organometallics. ,vol. 15, pp. 1087- 1089 ,(1996) , 10.1021/OM950833B
Takeshi Ohkuma, Hirohito Ooka, Shohei Hashiguchi, Takao Ikariya, Ryoji Noyori, PRACTICAL ENANTIOSELECTIVE HYDROGENATION OF AROMATIC KETONES Journal of the American Chemical Society. ,vol. 117, pp. 2675- 2676 ,(1995) , 10.1021/JA00114A043
Akio Fujii, Shohei Hashiguchi, Nobuyuki Uematsu, Takao Ikariya, Ryoji Noyori, Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using a Formic Acid−Triethylamine Mixture Journal of the American Chemical Society. ,vol. 118, pp. 2521- 2522 ,(1996) , 10.1021/JA954126L
Shohei Hashiguchi, Akio Fujii, Jun Takehara, Takao Ikariya, Ryoji Noyori, Asymmetric Transfer Hydrogenation of Aromatic Ketones Catalyzed by Chiral Ruthenium(II) Complexes Journal of the American Chemical Society. ,vol. 117, pp. 7562- 7563 ,(1995) , 10.1021/JA00133A037
Yoshiaki Nishibayashi, Kyohei Segawa, Jai Deo Singh, Shin-ichi Fukuzawa, Kouichi Ohe, Sakae Uemura, Novel Chiral Ligands, Diferrocenyl Dichalcogenides and Their Derivatives, for Rhodium- and Iridium-Catalyzed Asymmetric Hydrosilylation Organometallics. ,vol. 15, pp. 370- 379 ,(1996) , 10.1021/OM950533U
Pavel Krasik, Howard Alper, Schiff bases as added chiral ligands for the [Ru(η6-C6H6)Cl2]2 catalysed hydrogen-transfer reduction of ketones with 2-propanol Tetrahedron. ,vol. 50, pp. 4347- 4354 ,(1994) , 10.1016/S0040-4020(01)89371-6
Grazia Zassinovich, Roberto Bettella, Giovanni Mestroni, Nevenka Bresciani-Pahor, Silvano Geremia, Lucio Randaccio, Enantioselective hydrogen transfer reactions from propan-2-ol to ketones catalyzed by pentacoordinate iridium(I) complexes with chiral Schiff bases Journal of Organometallic Chemistry. ,vol. 370, pp. 187- 202 ,(1989) , 10.1016/0022-328X(89)87284-5
Patrick Gamez, Fabienne Fache, Pierre Mangeney, Marc Lamaire, Enantioselective catalytic reduction of ketones using C2-symmetric diamines as chiral ligands. Tetrahedron Letters. ,vol. 34, pp. 6897- 6898 ,(1993) , 10.1016/S0040-4039(00)91824-0
John M. Brown, Henri Brunner, Walter Leitner, Michael Rose, Enantioselective catalytic transfer hydrogenation of α,β-unsaturated carboxylic acids with formates catalyzed by novel ruthenium phosphine complexes☆ Tetrahedron-asymmetry. ,vol. 2, pp. 331- 334 ,(1991) , 10.1016/S0957-4166(00)82111-4
Yoshiaki Nishibayashi, Jai Deo Singh, Sakae Uemura, Shin-ichi Fukuzawa, Synthesis of chiral diferrocenyl diselenides and their application to asymmetric reactions Tetrahedron Letters. ,vol. 35, pp. 3115- 3118 ,(1994) , 10.1016/S0040-4039(00)76844-4