Synthesis of water-soluble aminosulfonamide ligands and their application in enantioselective transfer hydrogenation

作者: Christian Bubert , John Blacker , Stephen M Brown , John Crosby , Steven Fitzjohn

DOI: 10.1016/S0040-4039(01)00623-2

关键词: RutheniumTransfer hydrogenationEnantioselective synthesisBase (chemistry)ChemistryNoyori asymmetric hydrogenationWater solubleCatalysisSulfonic acidOrganic chemistry

摘要: Abstract Water-soluble analogues of Noyori's (1S,2S)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine and Knochel's (1R,2R)-N-(p-tolylsulfonyl)-1,2-diaminocyclohexane, containing an additional sulfonic acid group, have been synthesised. The ruthenium catalysed reduction aromatic ketones using enantiomerically pure catalyst derived from water soluble ligands [RuCl2(p-cymene)]2 has examined. High enantioselectivity moderate activity were observed in the 2-propanol/base system. addition is necessary to stabilise catalyst.

参考文章(15)
William Robert Hardy Hurtley, Samuel Smiles, CCXLI.—ortho-Dithiolbenzene Journal of The Chemical Society (resumed). ,vol. 129, pp. 1821- 1828 ,(1926) , 10.1039/JR9262901821
Louise Tonks, Michael S Anson, Klaus Hellgardt, Amin R Mirza, David F Thompson, Jonathan MJ Williams, Palladium catalysed heck reactions and allylic substitution reactions using glass bead technology Tetrahedron Letters. ,vol. 38, pp. 4319- 4322 ,(1997) , 10.1016/S0040-4039(97)00890-3
Amin R. Mirza, Michael S. Anson, Klaus Hellgardt, Matthew P. Leese, David F. Thompson, Louise Tonks, Jonathan M. J. Williams, Optimisation of Palladium-Based Supported Liquid-Phase Catalysts in the Heck Reaction Organic Process Research & Development. ,vol. 2, pp. 325- 331 ,(1998) , 10.1021/OP980030A
Michael S. Anson, Mathew P. Leese, Louise Tonks, Jonathan M. J. Williams, Transition metal catalysed reactions using glass bead technology Journal of the Chemical Society, Dalton Transactions. pp. 3529- 3538 ,(1998) , 10.1039/A802593B
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
Tim Thorpe, Stephen M Brown, John Crosby, Steven Fitzjohn, James P Muxworthy, Jonathan M.J Williams, A practical synthesis of a disulfonated phosphine and its application to biphasic catalysis Tetrahedron Letters. ,vol. 41, pp. 4503- 4505 ,(2000) , 10.1016/S0040-4039(00)00651-1
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
Ferenc Joó, Ágnes Kathó, Recent developments in aqueous organometallic chemistry and catalysis Journal of Molecular Catalysis A: Chemical. ,vol. 116, pp. 3- 26 ,(1997) , 10.1016/S1381-1169(96)00075-1
Kazuhiko Matsumura, Shohei Hashiguchi, Takao Ikariya, Ryoji Noyori, Asymmetric Transfer Hydrogenation of α, β-Acetylenic Ketones Journal of the American Chemical Society. ,vol. 119, pp. 8738- 8739 ,(1997) , 10.1021/JA971570A