Asymmetric Michael additions of α-nitrocyclohexanone to aryl nitroalkenes catalyzed by natural amino acid-derived bifunctional thioureas.

作者: Manuel Jörres , Ingo Schiffers , Iuliana Atodiresei , Carsten Bolm

DOI: 10.1021/OL302005F

关键词: CatalysisAmino acidThioureaBifunctionalArylOrganic chemistryChemistry

摘要: A series of new thiourea catalysts prepared from natural amino acids have been applied in organocatalytic asymmetric Michael additions α-nitrocyclohexanone to nitroalkenes. The resulting addition products are formed with excellent enantioselectivities (up an er 98:2) good yields 90%).

参考文章(59)
Zhi-wei Ma, Yu-xia Liu, Li-juan Huo, Xiang Gao, Jing-chao Tao, Doubly stereocontrolled asymmetric Michael addition of acetylacetone to nitroolefins promoted by an isosteviol-derived bifunctional thiourea Tetrahedron-asymmetry. ,vol. 23, pp. 443- 448 ,(2012) , 10.1016/J.TETASY.2012.03.020
Abigail G. Doyle, Eric N. Jacobsen, Small-molecule H-bond donors in asymmetric catalysis. Chemical Reviews. ,vol. 107, pp. 5713- 5743 ,(2007) , 10.1021/CR068373R
Peter R. Schreiner, Alexander Wittkopp, H-bonding additives act like Lewis acid catalysts. Organic Letters. ,vol. 4, pp. 217- 220 ,(2002) , 10.1021/OL017117S
Santanu Mukherjee, Jung Woon Yang, Sebastian Hoffmann, Benjamin List, Asymmetric enamine catalysis. Chemical Reviews. ,vol. 107, pp. 5471- 5569 ,(2007) , 10.1021/CR0684016
Roberto Ballini, Marino Petrini, Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) Tetrahedron. ,vol. 60, pp. 1017- 1047 ,(2004) , 10.1016/J.TET.2003.11.016
Magnus Rueping, Alejandro Parra, Uxue Uria, François Besselièvre, Estíbaliz Merino, Catalytic asymmetric domino Michael addition-alkylation reaction: enantioselective synthesis of dihydrofurans. Organic Letters. ,vol. 12, pp. 5680- 5683 ,(2010) , 10.1021/OL102499R
Diana Almaşi, Diego A. Alonso, Carmen Nájera, Organocatalytic asymmetric conjugate additions Tetrahedron-asymmetry. ,vol. 18, pp. 299- 365 ,(2007) , 10.1016/J.TETASY.2007.01.023
Xiu-Qin Dong, Huai-Long Teng, Min-Chao Tong, He Huang, Hai-Yan Tao, Chun-Jiang Wang, Organocatalytic asymmetric Michael addition of α-aryl cyclopentanones to nitroolefins for construction of adjacent quaternary and tertiary stereocenters Chemical Communications. ,vol. 46, pp. 6840- 6842 ,(2010) , 10.1039/C0CC01987A
José M. Andrés, Rubén Manzano, Rafael Pedrosa, Novel Bifunctional Chiral Urea and Thiourea Derivatives as Organocatalysts: Enantioselective Nitro‐Michael Reaction of Malonates and Diketones Chemistry: A European Journal. ,vol. 14, pp. 5116- 5119 ,(2008) , 10.1002/CHEM.200800633