Ionic liquid supported 4-HO-Pro-Val derived organocatalysts for asymmetric aldol reactions in the presence of water

被引:20
作者
Kucherenko, Alexander S. [1 ]
Perepelkin, Vasily V. [1 ]
Zhdankina, Galina M. [1 ]
Kryshtal, Galina V. [1 ]
Srinivasan, Easwar [2 ]
Inani, Heena [2 ]
Zlotin, Sergei G. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] Cent Univ Rajasthan, Sch Chem Sci & Pharm, NH-8 Bandarsindri, Distt Ajmer, Rajasthan, India
基金
俄罗斯基础研究基金会;
关键词
KINETIC RESOLUTION; PEPTIDE CATALYSTS; MICHAEL REACTIONS; CONTINUOUS-FLOW; EFFICIENT; PROLINE; NITROOLEFINS; 1,4-ADDITION; TRIPEPTIDES; DERIVATIVES;
D O I
10.1016/j.mencom.2016.09.007
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel (4R)-HO-(2S)-Pro-(S)-Val derivative tagged to 1-methyl-imidazolium cation and PF6- anion efficiently catalyzes asymmetric aldol reactions of cyclic ketones with aromatic aldehydes in aqueous environment to afford the corresponding aldols in high yield with moderate to high anti-diastereo- (dr up to 99 :1) and enantioselectivity (up to 98% ee). The catalyst was recycled 9 times in the same reaction without any decrease in selectivity values.
引用
收藏
页码:388 / 390
页数:3
相关论文
共 52 条
[1]   Histidine-Containing Peptide Catalysts Developed by a Facile Library Screening Method [J].
Akagawa, Kengo ;
Sakai, Nobutaka ;
Kudo, Kazuaki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (06) :1822-1826
[2]   Peptide-catalyzed kinetic resolution of planar-chiral metallocenes [J].
Akiyama, Midori ;
Akagawa, Kengo ;
Seino, Hidetake ;
Kudo, Kazuaki .
CHEMICAL COMMUNICATIONS, 2014, 50 (58) :7893-7896
[3]   Organic and hybrid molecular systems [J].
Ananikov, Valentine P. ;
Khokhlova, Elena A. ;
Egorov, Mikhail P. ;
Sakharov, Alexey M. ;
Zlotin, Sergei G. ;
Kucherov, Alexei V. ;
Kustov, Leonid M. ;
Gening, Marina L. ;
Nifantiev, Nikolay E. .
MENDELEEV COMMUNICATIONS, 2015, 25 (02) :75-82
[4]   Efficient Recovery and Reuse of an Immobilized Peptidic Organocatalyst [J].
Arakawa, Yukihiro ;
Wiesner, Markus ;
Wennemers, Helma .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1201-1206
[5]   Structural insight into the aggregation of L-prolyl dipeptides and its effect on organocatalytic performance [J].
Berdugo, Cristina ;
Escuder, Beatriu ;
Miravet, Juan F. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (02) :592-600
[6]   Water: the most versatile and nature's friendly media in asymmetric organocatalyzed direct aldol reactions [J].
Bhowmick, Sudipto ;
Mondal, Anirban ;
Ghosh, Ayndrila ;
Bhowmick, Kartick C. .
TETRAHEDRON-ASYMMETRY, 2015, 26 (21-22) :1215-1244
[7]   Tuning acid-base cooperativity to create next generation silica-supported organocatalysts [J].
Brunelli, Nicholas A. ;
Jones, Christopher W. .
JOURNAL OF CATALYSIS, 2013, 308 :60-72
[8]   Asymmetric catalysis: Resin-bound hydroxyprolylthreonine derivatives in enamine-mediated reactions [J].
Carpenter, Richard D. ;
Fettinger, James C. ;
Lam, Kit S. ;
Kurth, Mark J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (34) :6407-6410
[9]   Peptidomimetic organocatalysts: efficient Michael addition of ketones onto nitroolefins with very low catalyst loading [J].
Chandrasekhar, Srivari ;
Kumar, Chintakunta Praveen ;
Kumar, Togapur Pavan ;
Haribabu, Kothapalli ;
Jagadeesh, Bharatam ;
Lakshmi, Jerripothula K. ;
Mainkar, Prathama S. .
RSC ADVANCES, 2014, 4 (57) :30325-30331
[10]   The role of double hydrogen bonds in asymmetric direct aldol reactions catalyzed by amino amide derivatives [J].
Chen, Xiao-Hua ;
Yu, Jie ;
Gong, Liu-Zhu .
CHEMICAL COMMUNICATIONS, 2010, 46 (35) :6437-6448