欢迎登录材料期刊网

材料期刊网

高级检索

将水溶性手性二胺(S,S)-1,2-二苯基乙二胺二磺酸钠((S,S)-DPENDS)与钌膦配合物([RuCl_2(TPPTS)_2]_2)原位生成的催化剂用于催化水相中苄叉丙酮的不对称加氢反应.在优化条件下,羰基加氢产物4-苯基-3-丁烯-2-醇的选择性可达96.0%,对映选择性可达71.2%.经正己烷简单萃取后即可实现催化剂与加氢产物的分离,循环使用5次后,目标产物4-苯基-3-丁烯-2-醇选择性和对映选择性没有明显下降.

The asymmetric hydrogenation of benzalacctone catalyzed by ruthenium monophosphine complex RuCl_2(TPPTS)_2 [TPPTS =P(m-C_6H_4SO_3Na)_3] modified by (S,S)-DPENDS (disodium salt of sulfonated (S,S)-1,2-diphenyl-1,2-ethylene-diamine) was investigated in a water medium. Under the optimized conditions, a chemoselectivity of 96.0% for 4-phenyl-3-butene-2-ol and ee value of 71.2% were ob tained. The products could be easily obtained by simple extraction with n-hexane, and the catalyst could be reused five times without evident loss of catalytic activity and enantioselectivity.

参考文献

[1] Noyori R;Ohkuma T .[J].Pure and Applied Chemistry,1999,71:1493.
[2] 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.
[3] Ohkuma T;Ooka H;lkariya T;Noyori R .[J].Journal of the American Chemical Society,1995,117:10417.
[4] Lindner E.;Ghanem A.;Warad I.;Eichele K.;Mayer HA.;Schurig V. .Asymmetric hydrogenation of an alpha,beta-unsaturated ketone by diamine(ether-phosphine)ruthenium(II) complexes and lipase-catalyzed kinetic resolution: a consecutive approach[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2003(8):1045-1053.
[5] Peach P;Cross DJ;Kenny JA;Mann I;Houson I;Campbell L;Walsgrove T;Wills M .Asymmetric transfer hydrogenation of alpha,beta-unsaturated, alpha-tosyloxy and alpha-substituted ketones[J].Tetrahedron,2006(8):1864-1876.
[6] Ohkuma T;Hattori T;Ooka H;Inoue T Noyori R .[J].Organic Letters,2004,6:2681.
[7] Wu J;Ji J X;Guo R W;Yeung C H Chan A S C .[J].Chemistry-A European Journal,2003,9:2963.
[8] Burk M J;Hems W;Herzberg D;Malan C Zanotti-Gerosa A .[J].Organic Letters,2000,2:4173.
[9] Ngo H L;Hu A;Lin W B .[J].Tetrahedron Letters,2005,46:595.
[10] von Arx M;Mallat T;Baiker A .[J].Journal of Molecular Catalysis A:Chemical,1999,148:275.
[11] 明方永,王金波,付海燕,陈骏,陈华,李贤均.手性二胺修饰的Ru-TPP/γ-Al2O3催化苄叉丙酮不对称加氢反应[J].催化学报,2007(12):1057-1061.
[12] Ohkuma T;Takeno H;Honda Y;Noyori R .[J].Advanced Synthesis and Catalysis,2001,343:369.
[13] Comils B;Herrmann W A;Eckl R W .[J].Journal of Molecular Catalysis A:Chemical,1997,116:27.
[14] Kuntz E G .[J].Chemtech,1987,17:570.
[15] Lecomte L;Sinou D;Bakos J;Toth I Heil B .[J].Journal of Organometallic Chemistry,1989,370:277.
[16] Yonehara K;Hashizume T;Mori K;Ohe K Uemura S .[J].Journal of Organic Chemistry,1999,64:5593.
[17] Lamouille T;Saluzzo C;ter Halle R;le Guyader F Lemaire M .[J].Tetrahedron Letters,2001,42:663.
[18] Ferrand A.;Bruno M.;Tommasino ML.;Lemaire M. .Hydrophilic diamine ligands for catalytic asymmetric hydrogenation of C=O bonds[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2002(13):1379-1384.
[19] 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.
[20] 陈华 .[D].成都:四川大学,1999.
[21] Thorpe T;Brown S M;Crosby J;Fitzjohn S Muxworthy J P Williams J M J .[J].Tetrahedron Letters,2000,41:4503.
[22] Ma Y P;Liu H;Chen L;Cui X Zhu J E Deng J G .[J].Organic Letters,2003,5:2103.
[23] Fache E;Santini C;Senocq F;Basset J M .[J].Journal of Molecular Catalysis,1992,72:331.
[24] Hallman P S;Stephenson T A;Wilkinson G .[J].Inorganic Syntheses,1972,12:238.
[25] 王祥智;陈华;黎耀忠;李贤均 .[J].分子催化,1995,9:214.
[26] 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.
[27] Berger A.;Delgado MR.;Dupont J.;de Souza RF. .Ionic liquid-phase asymmetric catalytic hydrogenation: hydrogen concentration effects on enantioselectivity[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2001(13):1825-1828.
[28] 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.
[29] 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.
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:
  • 1
    0%
  • 2
    0%
  • 3
    0%
  • 4
    0%
  • 5
    0%