Heteroaromatic N-Oxides in Asymmetric Catalysis: A Review.

作者: Zuzanna Wrzeszcz , Renata Siedlecka

DOI: 10.3390/MOLECULES25020330

关键词: Nitroaldol reactionOrganosiliconChirality (chemistry)NucleophileOrganocatalysisMichael reactionEnantioselective synthesisCombinatorial chemistryPyridineChemistry

摘要: An increasing interest in the synthesis and use of optically active pyridine N-oxides as chiral controllers for asymmetric reactions has been observed last few years. Chiral heteroaromatic can work powerful electron-pair donors, providing suitable electronic environments transition state formed within reaction. The nucleophilicity oxygen atom N-oxides, coupled with a high affinity silicon to oxygen, represent ideal properties development synthetic methodology based on nucleophilic activation organosilicon reagents. application efficient organocatalysts allylation, propargylation, allenylation, ring-opening meso-epoxides, well ligands metal complexes catalyzing Michael addition or nitroaldol reaction, also be found literature. This review deals stereoselective applications how differentiating are correlated their structure. It contains more recent results, covering approximately ten All reported examples have divided into five classes, according chirality elements present basic molecular frameworks.

参考文章(75)
Zhili Peng, Norito Takenaka, Applications of helical-chiral pyridines as organocatalysts in asymmetric synthesis. Chemical Record. ,vol. 13, pp. 28- 42 ,(2013) , 10.1002/TCR.201200010
Filip Hessler, Aleš Korotvička, David Nečas, Irena Valterová, Martin Kotora, Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes European Journal of Organic Chemistry. ,vol. 2014, pp. 2543- 2548 ,(2014) , 10.1002/EJOC.201301899
Petr Koukal, Martin Kotora, Enantioselective Allylation of (2E,4E)‐2,4‐Dimethylhexadienal: Synthesis of (5R,6S)‐(+)‐Pteroenone Chemistry: A European Journal. ,vol. 21, pp. 7408- 7412 ,(2015) , 10.1002/CHEM.201500050
Oleg V. Larionov, David Stephens, Adelphe M. Mfuh, Hadi D. Arman, Anastasia S. Naumova, Gabriel Chavez, Behije Skenderi, Insights into the mechanistic and synthetic aspects of the Mo/P-catalyzed oxidation of N-heterocycles Organic and Biomolecular Chemistry. ,vol. 12, pp. 3026- 3036 ,(2014) , 10.1039/C4OB00115J
Yu-Ning Pei, Yu Deng, Jing-Liang Li, Li Liu, Hua-Jie Zhu, New chiral biscarboline N,N′-dioxide derivatives as catalyst in enantioselective reduction of ketoimines with trichlorosilane Tetrahedron Letters. ,vol. 55, pp. 2948- 2952 ,(2014) , 10.1016/J.TETLET.2014.03.100
Juncheng Yang, Sheng Chu, Yong Guo, Leilei Luo, Fei Kong, Ying Wang, Zhigang Zou, Hyperbranched polymeric N-oxide: a novel kind of metal-free photocatalyst Chemical Communications. ,vol. 48, pp. 3533- 3535 ,(2012) , 10.1039/C2CC30308F
Carsten Bolm, Catalysis with Organic Molecules: A Success Story in Modern Catalytic Chemistry Advanced Synthesis & Catalysis. ,vol. 346, pp. 1022- 1022 ,(2004) , 10.1002/ADSC.200404222
Andrei V Malkov, Mark Bell, Maxime Vassieu, Valeria Bugatti, Pavel Kočovský, New pyridine-derived N-oxides as chiral organocatalysts in asymmetric allylation of aldehydes Journal of Molecular Catalysis A-chemical. ,vol. 196, pp. 179- 186 ,(2003) , 10.1016/S1381-1169(02)00649-0