Asymmetric Michael Reaction of Acetaldehyde with Nitroolefins Catalyzed by Highly Water-Compatible Organocatalysts in Aqueous Media

被引：29

作者：

Qiao, Yupu ^{[1
]}

He, Junpeng ^{[1
]}

Ni, Bukuo ^{[1
]}

Headley, Allan D. ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 14-15期

关键词：

acetaldehyde; asymmetric synthesis; Michael reaction; water-compatible organocatalysts; ORGANIC-REACTIONS; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; CONJUGATE ADDITION; ALDOL REACTION; EFFICIENT ORGANOCATALYSTS; RECYCLABLE ORGANOCATALYST; IMINIUM ACTIVATION; MANNICH REACTION; ACID CATALYSTS; SOLVENT-FREE;

D O I：

10.1002/adsc.201200215

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel category of diarylprolinol silyl ether catalysts which contain different lengths of alkylamine tags, was designed and synthesized. These catalysts were used, along with benzoic acid as the co-catalyst, to catalyze the asymmetric Michael reaction of the highly reactive acetaldehyde with nitroolefins. For the reactions studied, this catalytic system exhibited high reactivity in brine without any organic solvents; good yields (3061%) and high enantioselectivities (8097% ee) for a wide variety of nitrostyrenes were obtained.

引用

页码：2849 / 2853

页数：5

共 50 条

[31] Phosphoramidites are efficient, green organocatalysts for the Michael reaction. Mechanistic insights into the phosphorus-catalyzed Michael reaction of alkynones and implications for asymmetric catalysis
Grossman, RB
Comesse, S
Rasne, RM
Hattori, K
Delong, MN
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03): : 871 - 874
[32] Protonated (S)-prolinamide derivatives-water compatible organocatalysts for direct asymmetric aldol reaction
Chimni, Swapandeep Singh
Singh, Sarbjit
Mahajan, Dinesh
TETRAHEDRON-ASYMMETRY, 2008, 19 (19) : 2276 - 2284
[33] Highly Diastereo- and Enantioselective Direct Aldol Reactions Promoted by Water-Compatible Organocatalysts Bearing Central and Axial Chiral Elements
Peng, Fang-Zhi
Shao, Zhi-Hui
Pu, Xue-Wei
Zhang, Hong-Bin
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) : 2199 - 2204
[34] Highly enantioselective Michael addition of cyclohexanone to nitroolefins catalyzed by pyrrolidine-based bifunctional benzoylthiourea in water
Wang, Zhen-Yu
Ban, Shu-Rong
Yang, Meng-Chen
Li, Qing-Shan
CHIRALITY, 2016, 28 (11) : 721 - 727
[35] Chiral Polyureas Derived Cinchona Alkaloids: Highly Efficient Bifunctional Organocatalysts for the Asymmetric Michael Addition Reaction
Abdelkawy, Mahmoud A.
Davin, Christopher
Aly, El-Saied A.
El-Badawi, Mahmoud A.
Itsuno, Shinichi
CHEMISTRYSELECT, 2021, 6 (43): : 11971 - 11979
[36] Structure-reactivity relationships of L-proline derived spirolactams and α-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins
Kelleher, Fintan
Kelly, Sinead
Watts, John
McKee, Vickie
TETRAHEDRON, 2010, 66 (19) : 3525 - 3536
[37] Highly diastereo- and enantioselective direct aldol reactions promoted by water-compatible organocatalysts bearing a pyrrolidinyl-camphor structural scaffold
Tzeng, Zheng-Hao
Chen, Hung-Yao
Reddy, Raju Jannapu
Huang, Ching-Ting
Chen, Kwunmin
TETRAHEDRON, 2009, 65 (15) : 2879 - 2888
[38] Jorgensen-Hayashi catalysts supported on poly(ethylene glycol)s as highly efficient and reusable organocatalysts for the enamine-catalyzed asymmetric Michael reaction
Xia, Ai-Bao
Zhang, Can
Zhang, Yan-Peng
Guo, Yan-Jun
Zhang, Xiao-Long
Li, Zhao-Bo
Xu, Dan-Qian
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (37) : 9593 - 9599
[39] Cesium fluoride catalyzed Aza-Michael addition reaction in aqueous media
Labade, Vilas B.
Pawar, Shivaji S.
Shingare, Murlidhar S.
MONATSHEFTE FUR CHEMIE, 2011, 142 (10): : 1055 - 1059
[40] Cesium fluoride catalyzed Aza-Michael addition reaction in aqueous media
Vilas B. Labade
Shivaji S. Pawar
Murlidhar S. Shingare
Monatshefte für Chemie - Chemical Monthly, 2011, 142 : 1055 - 1059

← 1 2 3 4 5 →