Efficient organocatalysts derived from simple chiral acyclic amino acids in asymmetric catalysis

作者: Zhuo Chai , Gang Zhao

DOI: 10.1039/C1CY00347J

关键词:

摘要: Chiral amino acids have played a key role in the development of organocatalysis from biomimetic concept to an independent methodology, together with metal catalysis and enzyme catalysis, comprising three major catalytic methodologies modern organic synthesis. As excellent pool for design organocatalysts, chiral two obvious advantages: ready availability usually affordable costs modular structures allowing facile tuning efficiency. Recently, bifunctional/multifunctional primary–secondary amines, tertiary amine–thioureas, aminophosphines easily prepared simple acyclic been developed as efficient organocatalysts various asymmetric reactions leading variety useful compounds. In this perspective, we present personal overview some these recent advances field based on our own research experience.

参考文章(91)
John B. Brazier, Nicholas C. O. Tomkinson, Secondary and Primary Amine Catalysts for Iminium Catalysis Topics in Current Chemistry. ,vol. 291, pp. 281- 347 ,(2010) , 10.1007/978-3-642-02815-1_28
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
Hitoshi Ube, Naoki Shimada, Masahiro Terada, Asymmetric Direct Vinylogous Aldol Reaction of Furanone Derivatives Catalyzed by an Axially Chiral Guanidine Base Angewandte Chemie. ,vol. 49, pp. 1858- 1861 ,(2010) , 10.1002/ANIE.200906647
Scott R. Gilbertson, Scott E. Collibee, Anton Agarkov, Asymmetric Catalysis with Libraries of Palladium β-Turn Phosphine Complexes Journal of the American Chemical Society. ,vol. 122, pp. 6522- 6523 ,(2000) , 10.1021/JA992306F
Mitsuhiro Ueda, Taichi Kano, Keiji Maruoka, Organocatalyzed direct asymmetric α-halogenation of carbonyl compounds Organic and Biomolecular Chemistry. ,vol. 7, pp. 2005- 2012 ,(2009) , 10.1039/B901449G
Benjamin List, Richard A. Lerner, Carlos F. Barbas, Proline-Catalyzed Direct Asymmetric Aldol Reactions Journal of the American Chemical Society. ,vol. 122, pp. 2395- 2396 ,(2000) , 10.1021/JA994280Y
Scott E. Denmark, John R. Heemstra, Gregory L. Beutner, Catalytic, Enantioselective, Vinylogous Aldol Reactions Angewandte Chemie. ,vol. 44, pp. 4682- 4698 ,(2005) , 10.1002/ANIE.200462338
Kazuaki Ishihara, Kazuhiko Nakano, Design of an Organocatalyst for the Enantioselective Diels−Alder Reaction with α-Acyloxyacroleins Journal of the American Chemical Society. ,vol. 127, pp. 10504- 10505 ,(2005) , 10.1021/JA053368A
Valérie Declerck, Jean Martinez, Frédéric Lamaty, aza-Baylis−Hillman Reaction Chemical Reviews. ,vol. 109, pp. 1- 48 ,(2009) , 10.1021/CR068057C