手性羰基铁体系催化酮的不对称氢转移氢化

化学学报 ›› 2004, Vol. 62 ›› Issue (18): 1745-1750. 上一篇下一篇

研究论文

手性羰基铁体系催化酮的不对称氢转移氢化

陈建珊, 陈玲玲, 邢雁, 陈贵, 沈伟艺, 董振荣, 李岩云, 高景星

厦门大学化学系, 固体表面物理化学国家重点实验室, 厦门, 361005

投稿日期:2004-03-29 修回日期:2004-06-04 发布日期:2014-02-17
通讯作者: 高景星,E-mail:cuihua@jingxian.xru.edu.cn E-mail:cuihua@jingxian.xru.edu.cn
基金资助:
国家自然科学基金(No.20373056)、福建省科技厅重大科技项目(No.2002F016)和福建省厦门市科技局重大科技项目(No.3502Z20021044)资助.

Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Chiral Carbonyl Iron Systems

CHEN Jian-Shan, CHEN Ling-Ling, XING Yan, CHEN Gui, SHEN Wei-Yi, DONG Zhen-Rong, LI Yan-Yun, GAO Jing-Xing

Department of Chemistry, State Key Laboratory for Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005

Received:2004-03-29 Revised:2004-06-04 Published:2014-02-17

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摘要/Abstract

手性羰基铁络合物很少被用于芳香酮的不对称氢转移氢化.利用不同的羰基铁络合物与手性双胺双膦配体现场络合,形成手性胺膦铁催化体系.考察了它们对多种芳香酮的不对称氢转移催化氢化性能.结果表明,三核的手性胺膦铁簇合物是催化芳香酮不对称氢转移氢化的较好体系.当用三核的铁簇合物[Et₃NH]⁺[HFe₃(CO)₁₁]^-体系催化1,1-二苯基丙酮的氢化时,最高可获得98%的对映选择性.通过现场红外光谱测定,揣测羰基铁簇合物Fe₃(CO)₁₂在催化反应过程中保持三核的簇合物的簇骼不变.

关键词: 羰基铁, 手性胺膦配体, 芳香酮, 不对称氢转移氢化

Chiral carbonyl iron systems have seldom been used in asymmetric transfer hydrogenation of aromatic ketones. In this study, new chiral iron catalytic systems were synthesized in situ from different carbonyl iron complexes with chiral diaminodiphosphine ligands, respectively. These catalytic systems have been used for the asymmetric transfer hydrogenation of various aromatic ketones under mild conditions. The results indicated that trinuclear iron complexes were the best systems for the reactions. When the [Et₃NH]⁺[HFe₃(CO)₁₁]^- as catalyst was used for asymmetric reduction of 1,1-diphenylacetone, high enantioselectivity up to 98% was achieved. Monitoring the reaction in situ by infrared spectroscopy, it could be conjectured that the carbonyl iron cluster Fe₃(CO)₁₂ kept its trinuclear skeleton unchanged during the catalytic reaction.

Key words: carbonyl iron, chiral diaminodiphosphine ligand, aromatic ketone, asymmetric transfer hydrogenation

引用此文

陈建珊, 陈玲玲, 邢雁, 陈贵, 沈伟艺, 董振荣, 李岩云, 高景星. 手性羰基铁体系催化酮的不对称氢转移氢化[J]. 化学学报, 2004, 62(18): 1745-1750.

CHEN Jian-Shan, CHEN Ling-Ling, XING Yan, CHEN Gui, SHEN Wei-Yi, DONG Zhen-Rong, LI Yan-Yun, GAO Jing-Xing. Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Chiral Carbonyl Iron Systems[J]. Acta Chimica Sinica, 2004, 62(18): 1745-1750.

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参考文献

[1] Noyori, R. Asymmetric Catalysis in Organic Synthesis, John Wiley, New York, 1994, pp. 1 ～ 82.
[2] Takaya, H.; Noyori, R. Catalytic Asymmetric Synthesis, Ed.:Ojima, I., VCH, Berlin, 1993, pp. 20～ 30.
[3] Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
[4] Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10,2045.
[5] Blaser, H. U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner,F.; Steiner, H.; Studer, M. Adv. Syrth. Catal. 2003, 345,103.
[6] Burk, M. Acc. Chem. Res. 2000, 33, 363.
[7] Blaser, H. U.; Brieden, W.; Pugin, B.; Spindler, F.;Studer, A.; Togni, A. Top. Catal. 2002, 19, 3.
[8] Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H.Chem. Commun. 1998, 2077.
[9] Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori,R. J. Am. Chem. Soc. 1995, 117, 7562.
[10] Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori,R. J. Am. Chen. Soc. 1996, 118, 2521.
[11] Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999,64, 2186.
[12] Touchard, F.; Bernard, M.; Fache, F.; Delbecq, F.; Guiral,V.; Sautet, P.; Lemaire, M. J. Organomet. Chem. 1998,567, 133.
[13] Newkome, G. R. Chem. Rev. 1993, 93, 2067.
[14] Jiang, Y.; Zhu, Q.; Zhang, X. Tetrahedron Lett. 1997, 38,215.
[15] Sablong, R.; Osborn, J. A. Tetrahedron Lett. 1996, 37, 4937.
[16] Rahmouni, N.; Osborn, J. A.; Cian, A. D.; Fischer, J.;Ezzamarty, A. Organometallics 1998, 17, 2470.
[17] Trost, B. M.; Patterson, D. E. J. Org. Chem. 1998, 63,1339.
[18] Kless, A.; Kadyrov, R.; Borner, A.; Holz, J.; Kagan, H. B.Tetrahedron Lett. 1995, 36, 4601.
[19] Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996,15, 1087.
[20] Gao, J. X.; Zhang, H.; Yi, X. D.; Xu, P. P.; Tang, C.L.; Wan, H. L.; Tsai, K. R.; Ikariya, T. Chirality 2000,12, 383.
[21] Zhang, H.; Yang, C. B.; Li, Y. Y.; Dong, Z. R.; Gao, J.X.; Nakamura, H.; Murata, K.; Ikariya, T. Chem. Commun.2003, (1), 142.
[22] Tang, C. L.; Li, Y. Y.; Pan, E. D.; Zhang, H.; Zhou, Z.H.; Gao, J. X. Acta Chim. Sinica 2001, 59, 1831 (in Chinese).(唐纯良,李岩云,潘恩德,章慧,周朝晖,高景星,化学学报,2001,59,1831.)
[23] Henry, F.; Holtzclow, J. R. Inorganic Synthesis, Vol. 8, John Wiley & Sons, New York, London, 1966, pp. 146～ 148.

手性羰基铁体系催化酮的不对称氢转移氢化

Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Chiral Carbonyl Iron Systems

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