Bifunctional Chiral Quaternary Ammonium Salt Catalysts: A Rapidly Emerging Class of Powerful Asymmetric Catalysts

作者: Johanna Novacek , Mario Waser

DOI: 10.1002/EJOC.201201425

关键词: AmmoniumSalt (chemistry)Organic chemistryEnantioselective synthesisBifunctionalElectrophileNucleophileCatalysisChirality (chemistry)Chemistry

摘要: Chiral quaternary ammonium salt catalysts have emerged as one of the outstanding catalytic principles over last decades. Their ability to activate nucleophiles in a noncovalent fashion makes them unique. However, years it has become obvious that variety difficult transformations activation and control alone does not result sufficient selectivities, same holds true for sole electrophiles by other motifs. Thus, use bifunctional most promising strategies carry out demanding reactions highly stereoselective under mild reaction conditions, many these are possible using methods. This review will highlight some impressive recent examples this field compare performances with those commonly employed ones.

参考文章(65)
Luca Bernardi, Eugenio Indrigo, Salvatore Pollicino, Alfredo Ricci, Organocatalytic trifluoromethylation of imines using phase-transfer catalysis with phenoxides. A general platform for catalytic additions of organosilanes to imines. Chemical Communications. ,vol. 48, pp. 1428- 1430 ,(2012) , 10.1039/C0CC05777K
Pablo Bernal, Rosario Fernández, José M. Lassaletta, Organocatalytic Asymmetric Cyanosilylation of Nitroalkenes Chemistry: A European Journal. ,vol. 16, pp. 7714- 7718 ,(2010) , 10.1002/CHEM.201001107
Rongjun He, Seiji Shirakawa, Keiji Maruoka, Enantioselective base-free phase-transfer reaction in water-rich solvent. Journal of the American Chemical Society. ,vol. 131, pp. 16620- 16621 ,(2009) , 10.1021/JA906821Y
Martin J. O'Donnell, Shengde Wu, John C. Huffman, A new active catalyst species for enantioselective alkylation by phase-transfer catalysis Tetrahedron. ,vol. 50, pp. 4507- 4518 ,(1994) , 10.1016/S0040-4020(01)89382-0
Claudia Del Fiandra, Linda Piras, Francesco Fini, Paolo Disetti, Maria Moccia, Mauro F. A. Adamo, Phase transfer catalyzed enantioselective cyclopropanation of 4-nitro-5-styrylisoxazoles Chemical Communications. ,vol. 48, pp. 3863- 3865 ,(2012) , 10.1039/C2CC30401E
Taichi Kano, Akihiro Yamamoto, Sunhwa Song, Keiji Maruoka, Catalytic asymmetric syntheses of isoxazoline-N-oxides under phase-transfer conditions Chemical Communications. ,vol. 47, pp. 4358- 4360 ,(2011) , 10.1039/C0CC05786J
Marco Bella, Sara Kobbelgaard, Karl Anker Jørgensen, Organocatalytic Regio- and Asymmetric C-Selective SNAr ReactionsStereoselective Synthesis of Optically Active Spiro-pyrrolidone-3,3‘-oxoindoles Journal of the American Chemical Society. ,vol. 127, pp. 3670- 3671 ,(2005) , 10.1021/JA050200G
Dieter Enders, Thanh Vinh Nguyen, Chiral quaternary phosphonium salts: a new class of organocatalysts Organic and Biomolecular Chemistry. ,vol. 10, pp. 5327- 5331 ,(2012) , 10.1039/C2OB25823D