Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide for Asymmetric Michael Addition Reactions of Aldehydes with Nitroolefins

被引：0

作者：

Omar, Emmy M. ^{[2
]}

Dhungana, Kritanjali ^{[1
]}

Headley, Allan D. ^{[1
]}

Rahman, Mohd Basyaruddin Abdul ^{[2
]}

机构：

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

[2] Univ Putra Malaysia, Dept Chem, Fac Sci, Upm Serdang 43400, Selangor, Malaysia

来源：

LETTERS IN ORGANIC CHEMISTRY | 2011年 / 8卷 / 03期

关键词：

Aldehydes; asymmetric catalysis; ionic liquid; michael addition; nitroolefins; EFFICIENT ORGANOCATALYSTS; CONJUGATE ADDITION; KETONES; CATALYSTS; NITROALKENES; STRATEGY; PROLINE;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A class of ionic liquid supported (ILS) (S)-pyrrolidine sulfonamide organocatalyst (1c), which was developed earlier in our lab, has been applied to a wider range of Michael addition reaction, involving various aryl-substituted nitroolefins and a series of aldehydes. Catalyst 1c catalyzes Michael additions in which only 2 equivalents of aldehydes to each equivalent of nitroolefin are required. With 10 mol% of ILS catalyst 1c loading, moderate to excellent yields (51-98%) with moderate enantioselectivities (28-83% ee) and high diastereoselectivities (syn/anti ratio up to 97/3) were obtained. Moreover, the catalyst 1c could be easily recycled and reused for at least 5 times with slightly reduced activities.

引用

页码：170 / 175

页数：6

共 50 条

[41] A development of a reusable copper supported imidazolium functionalized ionic liquid catalyzed asymmetric Michael addition reaction
Priya, Velumani Bharathi
Ramya, Subramani
Uthayanila, Selvarasu
Karthikeyan, Parasuraman
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2021, 98 (12)
[42] Self-assembled proline-amino thioureas as efficient organocatalysts for the asymmetric Michael addition of aldehydes to nitroolefins
Wang, Wan-Hui
Abe, Takeshi
Wang, Xiang-Bo
Kodama, Koichi
Hirose, Takuji
Zhang, Guang-You
TETRAHEDRON-ASYMMETRY, 2010, 21 (24) : 2925 - 2933
[43] Asymmetric aldol reactions in ketone/ketone systems catalyzed by ionic liquid-supported C2-symmetrical organocatalyst
Kochetkov, Sergei V.
Kucherenko, Alexander S.
Zlotin, Sergei G.
MENDELEEV COMMUNICATIONS, 2015, 25 (03) : 168 - 170
[44] Highly efficient asymmetric organocatalytic Michael addition of α,α-disubstituted aldehydes to nitroolefins under solvent-free conditions
He, Junpeng
Chen, Qiankun
Ni, Bukuo
TETRAHEDRON LETTERS, 2014, 55 (19) : 3030 - 3032
[45] Asymmetric Synthesis of Cyclic Nitrones via Organocatalytic Michael Addition of Aldehydes to Nitroolefins and Subsequent Reductive Cyclization.
Szczesniak, Piotr
Staszewska-Krajewska, Olga
Furman, Bartlomiej
Mlynarski, Jacek
CHEMISTRYSELECT, 2017, 2 (09): : 2670 - 2676
[46] Theoretical Study on the Asymmetric Michael Addition of Cyclohexanone with trans-β-Nitrostyrene Catalyzed by a Pyrrolidine-Type Chiral Ionic Liquid
Sun, Hui
Zhang, Dongju
Zhang, Changqiao
Liu, Chengbu
CHIRALITY, 2010, 22 (09) : 813 - 819
[47] Tripeptides as efficient asymmetric catalysts for 1,4-addition reactions of aldehydes to nitroolefins - A rational approach
Wiesner, Markus
Revell, Jefferson D.
Wennemers, Helma
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1871 - 1874
[48] Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by L-prolinamide derivatives using phenols as co-catalysts
Cheng, Yan-Qin
Bian, Zheng
He, Ya-Bing
Han, Fu-She
Kang, Chuan-Qing
Ning, Zhao-Lun
Gao, Lian-Xun
TETRAHEDRON-ASYMMETRY, 2009, 20 (15) : 1753 - 1758
[49] Structure-Reactivity Studies of Simple 4-Hydroxyprolinamide Organocatalysts in the Asymmetric Michael Addition Reaction of Aldehydes to Nitroolefins
Watts, John
Luu, Lien
McKee, Vickie
Carey, Ed
Kelleher, Fintan
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 1035 - 1042
[50] 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
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1147 - 1168

← 1 2 3 4 5 →