Design, synthesis and application of chiral tetraoxacalix[2]arene[2]triazine-based organocatalysts in asymmetric Michael addition reactions

被引：8

作者：

Genc, Hayriye Nevin ^{[1
]}

Ozgun, Ummu ^{[2
]}

Sirit, Abdulkadir ^{[2
]}

机构：

[1] Necmettin Erbakan Univ, Ahmet Kelesoglu Educ Fac, Dept Sci Educ, TR-42090 Konya, Turkey

[2] Necmettin Erbakan Univ, Ahmet Kelesoglu Educ Fac, Dept Chem, Konya, Turkey

来源：

CHIRALITY | 2019年 / 31卷 / 04期

关键词：

asymmetric synthesis; Michael addition; organocatalysis; stereoselectivity; tetraoxacalix[2]arene[2]triazine; HIGHLY EFFICIENT ORGANOCATALYSTS; CONJUGATE ADDITION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; PI INTERACTIONS; IONIC LIQUIDS; KETONES; NITROOLEFINS; DERIVATIVES; NITROALKENES; RECOGNITION;

D O I：

10.1002/chir.23055

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel type of oxacalix[2]arene[2]triazine-based organocatalysts for asymmetric Michael reactions are reported for the first time. Chiral subunits were attached to the heteroatom-bridged calixaromatic platform by a reaction of (R)- and (S)-1-aminotetraline with tetraoxacalix[2]arene[2]triazine in both enantiomeric forms. To evaluate the catalytic efficiency of the novel organocatalysts, isobutyraldehyde reacted with various substituted and unsubstituted aromatic trans-beta-nitrostyrenes in tetrahydrofuran (THF), leading to Michael adducts in excellent yields and enantioselectivites (up to 97% yield and 99% ee).

引用

页码：293 / 300

页数：8

共 50 条

[1] Chiral tetraoxacalix[2]arene[2]triazine-based organocatalysts for Enantioselective Aldol reactions
Genc, Hayriye Nevin
Ozgun, Ummu
Sirit, Abdulkadir
TETRAHEDRON LETTERS, 2019, 60 (27) : 1763 - 1768
[2] Effective asymmetric Michael addition of anthrone to nitroalkenes using chiral tetraoxacalix[2]arene[2]triazines as organocatalysts
Genc, Hayriye Nevin
CHIRALITY, 2019, 31 (09) : 711 - 718
[3] Enantioselective Michael reaction of anthrone catalyzed by chiral tetraoxacalix[2]arene[2]triazine derivatives
Genc, Hayriye Nevin
RSC ADVANCES, 2019, 9 (36) : 21063 - 21069
[4] Design and synthesis of novel chiral organocatalysts and their application in solvent-free asymmetric aldol and Michael reactions
Vega-Penaloza, Alberto
Avila-Ortiz, Claudia G.
Sanchez-Antonio, Omar
Juaristi, Eusebio
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[5] Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions
Felix, Ana Rita G.
Simoes, Pedro R. D.
Sousa, Francisco J. P. M.
Silva Serra, M. Elisa
Murtinho, Dina
LETTERS IN ORGANIC CHEMISTRY, 2020, 17 (05) : 372 - 380
[6] Synthesis and Functionalization of Inherently Chiral Tetraoxacalix[2]arene[2]pyridines
Pan, Shuai
Wang, De-Xian
Zhao, Liang
Wang, Mei-Xiang
ORGANIC LETTERS, 2012, 14 (24) : 6254 - 6257
[7] Asymmetric Synthesis of Inherently Chiral Tetraoxacalix[2]arene[2]pyridines via SNAr-Based Cross-Cyclotetramerization
Ibragimova, Regina
Lu, Qiu-Lin
Wang, Mei-Xiang
Zhu, Jieping
Tong, Shuo
CHEMISTRY-AN ASIAN JOURNAL, 2025,
[8] Novel chiral Tetraazacalix[4]arene[2]triazine-based derivatives as catalysts: enantioselective Michael reaction of nitroolefins and diketones
Genc, Hayriye Nevin
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2023, 103 (5-6) : 189 - 199
[9] Novel chiral Tetraazacalix[4]arene[2]triazine-based derivatives as catalysts: enantioselective Michael reaction of nitroolefins and diketones
Hayriye Nevin Genc
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2023, 103 : 189 - 199
[10] Synthesis of an Inherently Chiral Calix[4]arene Amino Acid and Its Derivatives: Their Application to Asymmetric Reactions as Organocatalysts
Shirakawa, Seiji
Shimizu, Shoichi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) : 1916 - 1924

← 1 2 3 4 5 →