以L-脯氨酸支载在功能化离子液体四氟硼酸1-(2-羟乙基)3.甲基咪唑鎓盐上的离子液体([Promim] CF3CO2)为催化剂兼溶剂,可在温和条件下顺利地催化硝基乙烷、硝基甲烷和各种醛的Henry缩合反应,目标产物的产率达79%~ 95%,非对映选择性可达3∶1,对映选择性可达85% ee.反应操作和后处理简单方便.[Promim] CF3CO2离子液体通过简单的处理即可实现循环利用,以邻-硝基苯甲醛和硝基乙烷为反应底物的模板反应,这种离子液体可以较稳定地循环使用6次,催化活性不降.
参考文献
[1] | GONG Kai,FANG Dong,SHI Qunrong,et al.Knoevenagel Condensation Reaction Catalyzed by Functionalized Ionic Liquid[J].Chinese J Appl Chem,2007,24 (9):1089-1091 (in Chinese).巩凯,方东,施群荣,等.碱性功能离子液体催化Knoevenagel缩合反应[J].应用化学,2007,24(9):1089-1091. |
[2] | David C F,Amanda M L,Doug W M.The Knoevenagel Reaction:Analysis and Recycling of the Ionic Liquid Medium[J].Tetrahedron Lett,2006,47 (11):1699-1703. |
[3] | Miao W S,Chan T H.Ionic-liquid-supported Organocatalyst:Efficient and Recyclable Ionic-Liquid-Anchored Proline for Asymmetric Aldol reaction[J].Adv Synth Catal,2006,248(12/13):1711-1718. |
[4] | Luo S Z,Mi X L,Ahang L,et al.Functionalized Chiral Ionic Liquids as Highly Efficient Asymmetric Organocatalysts for Michael Addition to Nitroolefins[J].Angew Chem Int Ed,2006,45(19):3093-3097. |
[5] | Sasai H,Shibasaki M.Catalytic Asymmetric Nitroaldol Reaction:An Efficient Synthesis of (S)-Propranolol Using the Lanthanum Binaphthol Complex[J].Tetrahedron Lett,1993,34(5):855-858. |
[6] | Sasai H,Shibasaki M.Syntheses of (S)-(-)-pindolol and[3'-13 C]-(R)-(-)-pindolol Utilizing a Lanthanum-lithium(R)-BINOL[(R)-LLB]Catalyzed Nitroaldol Reaction[J].Tetrahedron,1994,50(43):12313-12318. |
[7] | Takaoka E,Shibasaki M.Catalytic Asymmetric Synthesis of Arbutamine[J].Hereocydes,1997,46:157-163 |
[8] | Corey E J,Zhang F Y.Re-and Si-face-selective Nitroaidol Reactions Catalyzed by a Rigid Chiral Quaternary Ammonium Salt:a Highly Stereo-selective Synthesis of the HIV Protease Inhibitor Amprenavir(Vertex 478)[J].Angew Chem Int Ed,1999,38(13/14):1931-1933. |
[9] | Chen Z,Li Y,Xie H,et al.Ionic-liquid-supported Proline as a Catalyst for Direct Asymmetric Aldol Reaction[J].Russ J Org Chem,2008,44(12):1807-1810. |
[10] | CHEN Xuewei,LI Xuehui,SONG Hongbing,et al.Synthesis of a Basic Imidazolide Ionic Liquid and Its Application in Catalyzing Knoevenagel Condensation[J].Chinese J Catal,2008,29(10):957-959 (in Chinese).陈学伟,李雪辉,宋红兵,等.咪唑阴离子型碱性离子液体的合成及其催化Knoevenagel缩合反应[J].催化学报,2008,29(10):957-959. |
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%