Design and synthesis of (S)- and (R)-α-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of α-amino acids

作者: Ryosuke Takeda , Akie Kawamura , Aki Kawashima , Hiroki Moriwaki , Tatsunori Sato

DOI: 10.1039/C4OB00669K

关键词: ReagentChiral auxiliaryAmino acidEthylamineOrganic chemistryCost structureChemistryPhysical and Theoretical ChemistryBiochemistry

摘要: This work presents the first chemical approach for resolution of α-amino acids offering following advantages: (1) The specially designed resolving reagent is derived from α-(phenyl)ethylamine, most inexpensive chiral auxiliary, which can be recycled and reused, rendering cost structure complete process very attractive; (2) time-efficient two-step conducted under operationally convenient conditions with virtually quantitative yields; (3) readily adapted to large-scale use.

参考文章(95)
Fleur Drouet, Anaïs F. M. Noisier, Craig S. Harris, Daniel P. Furkert, Margaret A. Brimble, A Convenient Method for the Asymmetric Synthesis of Fluorinated α‐Amino Acids from Alcohols European Journal of Organic Chemistry. ,vol. 2014, pp. 1195- 1201 ,(2014) , 10.1002/EJOC.201301718
Mackenzie Bergagnini, Kazunobu Fukushi, Jianlin Han, Norio Shibata, Christian Roussel, Trevor K. Ellis, José Luis Aceña, Vadim A. Soloshonok, NH-type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications Organic and Biomolecular Chemistry. ,vol. 12, pp. 1278- 1291 ,(2014) , 10.1039/C3OB41959B
Jun-An Ma, Recent Developments in the Catalytic Asymmetric Synthesis of α- and β-Amino Acids Angewandte Chemie International Edition. ,vol. 42, pp. 4290- 4299 ,(2003) , 10.1002/ANIE.200301600
Vadim A Soloshonok, Dimitry V Avilov, Valery P Kukhar', Vitali I Tararov, Tatiana F Savel'eva, Tatiana D Churkina, Nicolai S Ikonnikov, Konstantin A Kochetkov, Svetlana A Orlova, Alexander P Pysarevsky, Yuri T Struchkov, Nikolai I Raevsky, Yuri N Belokon', Asymmetric aldol reactions of chiral Ni(II)-complex of glycine with aliphatic aldehydes. Stereodivergent synthesis of syn-(2S)- and syn-(2R)-β-alkylserines Tetrahedron-asymmetry. ,vol. 6, pp. 1741- 1756 ,(1995) , 10.1016/0957-4166(95)00220-J
Hiroki Moriwaki, Daniel Resch, Hengguang Li, Iwao Ojima, Ryosuke Takeda, José Luis Aceña, Vadim Soloshonok, Inexpensive chemical method for preparation of enantiomerically pure phenylalanine Amino Acids. ,vol. 46, pp. 945- 952 ,(2014) , 10.1007/S00726-013-1656-0
José Luis Aceña, Alexander E. Sorochinsky, Hiroki Moriwaki, Tatsunori Sato, Vadim A. Soloshonok, Synthesis of fluorine-containing α-amino acids in enantiomerically pure form via homologation of Ni(II) complexes of glycine and alanine Schiff bases Journal of Fluorine Chemistry. ,vol. 155, pp. 21- 38 ,(2013) , 10.1016/J.JFLUCHEM.2013.06.004
Yuri N. Belokon', Vitali I. Tararov, Viktor I. Maleev, Tatiana F. Savel'eva, Michael G. Ryzhov, Improved procedures for the synthesis of (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB) and Ni(II) complexes of Schiff's bases derived from BPB and amino acids Tetrahedron: Asymmetry. ,vol. 9, pp. 4249- 4252 ,(1998) , 10.1016/S0957-4166(98)00449-2