Design, synthesis, and application of tartaric acid derived N-spiro quaternary ammonium salts as chiral phase-transfer catalysts
作者： Mario Waser , Katharina Gratzer , Richard Herchl , Norbert Müller
DOI: 10.1039/C1OB06573D
关键词: Chemistry 、 Molecule 、 Design synthesis 、 Tartaric acid 、 Chiral phase 、 Ammonium 、 Glycine 、 Catalysis 、 Organic chemistry
摘要: A novel class of tartaric acid-derived N-spiro quaternary ammonium salts was synthesised starting from known TADDOLs. These compounds were found to catalyse the asymmetric α-alkylation glycine Schiff bases with high enantioselectivities and in good yields.
rsc.org
sci-hub.se 参考文章(35)
Handbook of phase transfer catalysis Blackie Academic & Professional. ,(1997) , 10.1007/978-94-009-0023-3
Paul Le Maux, Viviane Massonneau, Gérard Simonneaux, Catalytic asymmetric syntheses. Tetrahedron. ,vol. 44, pp. 1409- 1412 ,(1988) , 10.1016/S0040-4020(01)85919-6
Mario Waser, Manuela Haunschmidt, Markus Himmelsbach, A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions. Monatshefte Fur Chemie. ,vol. 141, pp. 1347- 1351 ,(2010) , 10.1007/S00706-010-0410-5
R. Helder, J.C. Hummelen, R.W.P.M. Laane, J.S. Wiering, Hans Wynberg, Catalytic asymmetric induction in oxidation reactions. The synthesis of optically active epoxides. Tetrahedron Letters. ,vol. 17, pp. 1831- 1834 ,(1976) , 10.1016/S0040-4039(00)93796-1
Ulf H. Dolling, Paul Davis, Edward J. J. Grabowski, Efficient catalytic asymmetric alkylations. 1. Enantioselective synthesis of (+)-indacrinone via chiral phase-transfer catalysis Journal of the American Chemical Society. ,vol. 106, pp. 446- 447 ,(1984) , 10.1021/JA00314A045
Sanjeev Kumar, Uma Ramachandran, None, The synthesis and applications of asymmetric phase-transfer catalysts derived from isomannide and isosorbide Tetrahedron. ,vol. 61, pp. 4141- 4148 ,(2005) , 10.1016/J.TET.2005.02.010
Martin J. O'Donnell, William D. Bennett, Shengde Wu, The stereoselective synthesis of .alpha.-amino acids by phase-transfer catalysis Journal of the American Chemical Society. ,vol. 111, pp. 2353- 2355 ,(1989) , 10.1021/JA00188A089
Takuya Hashimoto, Keiji Maruoka, Recent development and application of chiral phase-transfer catalysts. Chemical Reviews. ,vol. 107, pp. 5656- 5682 ,(2007) , 10.1021/CR068368N
Quan Lan, Xisheng Wang, Seiji Shirakawa, Keiji Maruoka, Phase-Transfer Catalyzed Asymmetric Conjugate Additions of β-Ketoesters to Acetylenic Ketones Organic Process Research & Development. ,vol. 14, pp. 684- 686 ,(2010) , 10.1021/OP100014V
Scott E. Denmark, Nathan D. Gould, Larry M. Wolf, None, A Systematic Investigation of Quaternary Ammonium Ions as Asymmetric Phase-Transfer Catalysts. Synthesis of Catalyst Libraries and Evaluation of Catalyst Activity The Journal of Organic Chemistry. ,vol. 76, pp. 4260- 4336 ,(2011) , 10.1021/JO2005445