在聚乙二醇-400-水介质中,以(1S,2S)-1,2-二苯基乙二胺的磺酸钠盐为手性修饰剂,考察了水溶性三(间-磺酸钠苯基)膦稳定的Ru催化苯乙酮及其衍生物的不对称加氢反应.结果表明,该催化剂体系具有良好的催化活性和对映选择性.在优化反应条件下,苯乙酮转化率和对映选择性分别为100％和84.9％.经正己烷萃取后,催化剂即可从产物中分离出来,并可重复使用多次.
参考文献
| [1] | Ohkuma T.;Doucet H.;Pham T.;Kozawa M.;Murata K.;Katayama E.;Yokozawa T.;Ikariya T.;Noyori R.;Koizumi M. .Asymmetric hydrogenation of alkenyl, cyclopropyl, and aryl ketones. RuCl2(xylbinap)(1,2-diamine) as a precatalyst exhibiting a wide scope[J].Journal of the American Chemical Society,1998(51):13529-13530. |
| [2] | Ohkuma T.;Takeno H.;Noyori R.;Ishii D. .Asymmetric hydrogenation of amino ketones using chiral RuCl2(diphophine)(1,2-diamine) complexes[J].Journal of the American Chemical Society,2000(27):6510-6511. |
| [3] | Ohkuma T;Koizumi M;Muniz K;Hilt G Kabuto C Noyori R .[J].Journal of the American Chemical Society,2002,124:6508. |
| [4] | Ngo H L;Hu A;Lin W .[J].Tetrahedron Letters,2005,46:595. |
| [5] | Pu L. .1,1 '-binaphthyl dimers, oligomers, and polymers: Molecular recognition, asymmetric catalysis, and new materials [Review][J].Chemical Reviews,1998(7):2405-2494. |
| [6] | Fan Q H;Li Y M;Chan A S C .[J].Chemical Reviews,2002,102:3385. |
| [7] | Guernik S;Wolfson A;Herskowitz M;Greenspoon N,Geresh S.[J].Chemical Communications,2001:2314. |
| [8] | Brown R A;Pollet P;Mckoon E;Eckert C A Liotta C L Jessop P G .[J].Journal of the American Chemical Society,2001,123:1254. |
| [9] | Zhu Y H;Carpenter K;Bun C C;Bahnmueller S,Chan P,Srid V S,Kee L W,Hawthorne M F .[J].Angewandte Chemie International Edition,2003,42:3792. |
| [10] | Ngo H L;HuA;Lin W.[J].Chemical Communications,2003:1912. |
| [11] | Hu A;Ngo H L;Lin W .[J].Angewandte Chemie International Edition,2004,43:2501. |
| [12] | Lam K H;Xu L J;Feng L C;Ruan J W Fan Q H Chan A S C .[J].Canadian Journal of Chemistry,2005,83:903. |
| [13] | Nasar K;Fache F;Lemaire M;Draye M Béziat J C Besson M Galez P .[J].Journal of Molecular Catalysis,1994,87:107. |
| [14] | BKnnemann H;Braun GA .[J].Chemistry-A European Journal,1997,3:1200. |
| [15] | Zuo X;Liu H;Guo D;Yang X .[J].Tetrahedron,1999,55:7787. |
| [16] | Studer M;Blaser H U;Exner C .[J].Advanced Synthesis and Catalysis,2003,345:45. |
| [17] | Tamura M;Fujihara H .[J].Journal of the American Chemical Society,2003,125:15742. |
| [18] | Jansat S;Gomez M;Philippot K;Muller G Guiu E Claver C Castillon S Chaudret B .[J].Journal of the American Chemical Society,2004,126:1592. |
| [19] | Astruc D;Lu F;Aranzaes J R .[J].Angewandte Chemie International Edition,2005,44:7852. |
| [20] | 王金波,明方永,蒋维东,樊光银,刘德蓉,陈华,李贤均.离子液体介质中钌纳米粒子催化苯乙酮及其衍生物的不对称加氢反应[J].物理化学学报,2007(09):1381-1386. |
| [21] | 刘德蓉,熊伟,杨朝芬,王金波,陈华,李瑞祥,李贤均.（1S,2S）-DPEN修饰的负载型钌-铑双金属催化剂催化苯乙酮及其衍生物的不对称加氢[J].物理化学学报,2007(04):479-483. |
| [22] | 姜和,王金波,熊伟,贾云,秦瑞香,刘德蓉,陈华.RuC1_2[（S）-P-Phos]-[（S）-DAIPEN]催化芳香酮的不对称加氢反应[J].物理化学学报,2010(03):675-678. |
| [23] | 王金波,秦瑞香,熊伟,贾云,刘德蓉,冯建,陈华.水相中RuCl_2（TPPTS）_2-（S,S）-DPENDS催化苄叉丙酮的不对称加氢反应[J].催化学报,2010(03):273-277. |
| [24] | Wang JB;Qin RX;Fu HY;Chen J;Feng J;Chen H;Lia XJ .Asymmetric hydrogenation of alpha,beta-unsaturated ketones catalyzed by Ru-TPPTS-(S,S)-DPENDS complex in ionic liquids[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2007(7):847-851. |
| [25] | Wang J B;Feng J;Qin R X;Fu H Y Yuan M L Chen H Li X J .[J].TETRAHEDRON-ASYMMETRY,2007,18:1643. |
| [26] | Tang B;Xiong W;Liu ER;Jia Y;Wang JB;Chen H;Li XJ .Asymmetric hydrogenation of aromatic ketones catalyzed by (1S,2S)-DPEN-modified Ru-PPh3/gamma-Al2O3 catalyst[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2008(11):1397-1401. |
| [27] | Andrade CKZ;Alves LM .Environmentally benign solvents in organic synthesis: Current topics[J].Current organic chemistry,2005(2):195-218. |
| [28] | Chen J;Spear S K;Hunddleston J G;Rogers R D .[J].Green Chemistry,2005,7:64. |
| [29] | Reetz MT;Wiesenhofer W .Liquid poly(ethylene glycol) and supercritical carbon dioxide as a biphasic solvent system for lipase-catalyzed esterification[J].Chemical communications,2004(23):2750-2751. |
| [30] | Chandrasekhar S;Narsihmulu C;Reddy N R;Sultana S S .[J].Tetrahedron Letters,2004,45:4581. |
| [31] | Xu L J;Lam K H;Ji J X;Wu J,Fan Q H,Lo W H,Chan A S C.[J].Chemical Communications,2005:1390. |
| [32] | Zhou HF;Fan QH;Tang WJ;Xu LJ;He YM;Deng GJ;Zhao LW;Gu LQ;Chan ASC .Polyethylene glycol as an environmentally friendly and recyclable reaction medium for enantioselective hydrogenation[J].Advanced synthesis & catalysis,2006(15):2172-2182. |
| [33] | Zhou H F;Fan Q H;Huang Y Y;Wu L He Y M Tang W J Gu L Q Chan A S C .[J].Journal of Molecular Catalysis A:Chemical,2007,275:47. |
| [34] | Zhou Z Q;Sun Y .[J].React Kinet Mech Catal,2010,99:391. |
| [35] | 陈华;刘海超;黎耀忠;程溥明 李贤均 .[J].分子催化,1994,8:124. |
| [36] | Thorpe T;Brown S M;Crosby J;Fitzjohn S Muxworthy J P Williams J M .[J].Tetrahedron Letters,2000,41:4503. |
| [37] | Ma Y P;Liu H;Chen L;Cui X Zhu J Deng J G .[J].Organic Letters,2003,5:2103. |
| [38] | Pugin B;Studer M;Kuesters E;Sedelmeier G;Feng X .Mixtures of ionic liquids and water as a medium for efficient enantioselective hydrogenation catalyst recycling[J].Advanced synthesis & catalysis,2004(12):1481-1486. |
| [39] | Laghmari M;Sinou D .[J].Journal of Molecular Catalysis,1991,66:L15. |
| [40] | Sandoval C A;Ohkuma T;Munlz K;Noyori R .[J].Journal of the American Chemical Society,2003,125:13490. |
| [41] | 熊伟,杨朝芬,袁茂林,陈华,李贤均.水/有机两相体系中钌膦配合物催化苯乙酮及其衍生物的不对称加氢反应[J].催化学报,2005(12):1093-1098. |
| [42] | Xiong W;Lin Q;Ma HX;Zheng HJ;Chen H;Li XJ .Asymmetric hydrogenation of aromatic ketones in ionic-liquid media catalyzed by Ru-TPPTS-(1S,2S)-DPENDS complexes[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2005(11):1959-1962. |
| [43] | Noyori R;Ohkuma T .[J].Angewandte Chemie International Edition,2001,40:40. |
| [44] | Kamaluddin A R;Faatz M;Alan A J;Morris R H .[J].Journal of the American Chemical Society,2001,123:7473. |
| [45] | Liu D R;Xiong W;Fan G Y;Chen H Li R X Li X J .[J].Applied Catalysis A:General,2008,339:93. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%