Functionalized chiral ionic liquid as recyclable organocatalyst for asymmetric Michael addition to nitrostyrenes

被引：114

作者：

Ni, Bukuo ^{[1
]}

Zhang, Qianying ^{[1
]}

Headley, Allan D. ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, Commerce, TX 75429 USA

来源：

GREEN CHEMISTRY | 2007年 / 9卷 / 07期

关键词：

D O I：

10.1039/b702081c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new type of pyrrolidine-based chiral ionic liquid has been developed. This chiral ionic liquid was found to catalyze the Michael addition reaction of aldehydes and nitrostyrenes to give moderate yields, good enantioselectivies, high diastereoselectivities, and recyclability.

引用

页码：737 / 739

页数：3

共 35 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
Alexakis, A
Andrey, O
[J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
[2] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins
Andrey, O
Alexakis, A
Tomassini, A
Bernardinelli, G
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1147 - 1168
[3] Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin
Andrey, O
Vidonne, A
Alexakis, A
[J]. TETRAHEDRON LETTERS, 2003, 44 (43) : 7901 - 7904
[4] Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis
Baudequin, C
Brégeon, D
Levillain, J
Guillen, F
Plaquevent, JC
Gaumont, AC
[J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (24) : 3921 - 3945
[5] Ionic liquids and chirality: opportunities and challenges
Baudequin, C
Baudoux, J
Levillain, J
Cahard, D
Gaumont, AC
Plaquevent, JC
[J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (20) : 3081 - 3093
[6] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins
Betancort, JM
Sakthivel, K
Thayumanavan, R
Tanaka, F
Barbas, CF
[J]. SYNTHESIS-STUTTGART, 2004, (09): : 1509 - 1521
[7] Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins
Cao, Chun-Li
Ye, Meng-Chun
Sun, Xiu-Li
Tang, Yong
[J]. ORGANIC LETTERS, 2006, 8 (14) : 2901 - 2904
[8] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
Cobb, AJA
Shaw, DM
Longbottom, DA
Gold, JB
Ley, SV
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) : 84 - 96
[9] 5-Pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nitro-olefins
Cobb, AJA
Longbottom, DA
Shaw, DM
Ley, SV
[J]. CHEMICAL COMMUNICATIONS, 2004, (16) : 1808 - 1809
[10] N-arenesulfonyl-2-aminomethylpyrrolidines -: Novel modular ligands and organocatalysts for asymmetric catalysis
Dahlin, N
Bogevig, A
Adolfsson, H
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1101 - 1105

← 1 2 3 4 →