Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide, a Recyclable Organocatalyst for the Highly Enantioselective Michael Addition to Nitroolefins

被引：102

作者：

Ni, Bukuo ^{[1
]}

Zhang, Qianying ^{[1
]}

Dhungana, Kritanjali ^{[1
]}

Headley, Allan D. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

基金：

美国国家科学基金会;

关键词：

ASYMMETRIC CONJUGATE ADDITION; KETONES; ALDEHYDES; CATALYSTS; NITROSTYRENES; NITROALKANES; DERIVATIVES;

D O I：

10.1021/ol900003e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new class of ionic liquid supported (ILS) (S)-pyrrolidine sulfonamide organocatalyst has been developed and shown to be a very effective catalyst for the asymmetric Michael addition reactions of ketones and aldehyde to nitroolefins with high enantio- and diastereoselectivities. This ILS organocatalyst is also easily recycled and could be reused at least five times without significant loss of its ability to affect the outcome of the asymmetric reactions.

引用

页码：1037 / 1040

页数：4

共 51 条

[21] A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions
Ishii, T
Fujioka, S
Sekiguchi, Y
Kotsuki, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9558 - 9559
[22] Amino acids and peptides as asymmetric organocatalysts
Jarvo, ER
Miller, SJ
[J]. TETRAHEDRON, 2002, 58 (13) : 2481 - 2495
[23] Krause N, 2001, SYNTHESIS-STUTTGART, P171
[24] Highly enantioselective conjugate addition of malonate and β-ketoester to nitroalkenes:: Asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids
Li, HM
Wang, Y
Tang, L
Deng, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) : 9906 - 9907
[25] Polymer-immobilized pyrrolidine-based chiral ionic liquids as recyclable organocatalysts for asymmetric Michael additions to nitrostyrenes under solvent-free reaction conditions
Li, Pinhua
Wang, Lei
Wang, Min
Zhang, Yicheng
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (07) : 1157 - 1160
[26] Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins
List, B
Pojarliev, P
Martin, HJ
[J]. ORGANIC LETTERS, 2001, 3 (16) : 2423 - 2425
[27] Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for Michael addition to nitroolefins
Luo, Sanzhong
Mi, Xueling
Zhang, Long
Liu, Song
Xu, Hui
Cheng, Jin-Pei
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) : 3093 - 3097
[28] Organocatalytic direct Michael reaction of ketones and aldehydes with β-nitrostyrene in brine
Mase, N
Watanabe, K
Yoda, H
Takabe, K
Tanaka, F
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) : 4966 - 4967
[29] Direct asymmetric organocatalytic Michael reactions of α,α-disubstituted aldehydes with β-nitrostyrenes for the synthesis of quaternary carbon-containing products
Mase, N
Thayumanavan, R
Tanaka, F
Barbas, CF
[J]. ORGANIC LETTERS, 2004, 6 (15) : 2527 - 2530
[30] Direct enantioselective Michael addition of aldehydes to vinyl ketones catalyzed by chiral amines
Melchiorre, P
Jorgensen, KA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) : 4151 - 4157

← 1 2 3 4 5 6 →