Studies on the true catalyst in the phosphate-promoted desymmetrization of meso-aziridines with silylated nucleophiles
作者： Giorgio Della Sala
DOI: 10.1016/J.TET.2012.10.068
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摘要: Abstract Significant amounts of metal phosphate impurities have been detected by NMR spectroscopy and ICP-OES analysis synthetic, as well purchased, samples VAPOL hydrogen purified on silica gel. The previously reported phosphate-catalyzed desymmetrization meso-aziridines with different silylated compounds, has re-examined. While metal-free phosphoric acid exhibited low activity enantioselectivity, calcium magnesium salts proved to be the true catalysts in these related processes. Reproducible high enantioselectivities were obtained ring-opening cyclic Me3SiX (X=SPh, SePh, N3) employing a 1:1 mixture phosphates. reaction successfully extended Me3SiSBn, Me3SiSMe Me3SiNCS, giving ring-opened products yield unprecedented moderate good enantioselectivities.
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sci-hub.se 参考文章(58)
Yantao Zhu, Matt D. Gieselman, Hao Zhou, Olga Averin, Wilfred A. van der Donk, Biomimetic studies on the mechanism of stereoselective lanthionine formation Organic and Biomolecular Chemistry. ,vol. 1, pp. 3304- 3315 ,(2003) , 10.1039/B304945K
Wenhua Zheng, Zuhui Zhang, Matthew J. Kaplan, Jon C. Antilla, Chiral Calcium VAPOL Phosphate Mediated Asymmetric Chlorination and Michael Reactions of 3-Substituted Oxindoles Journal of the American Chemical Society. ,vol. 133, pp. 3339- 3341 ,(2011) , 10.1021/JA109824X
Jian Lv, Xin Li, Long Zhong, Sanzhong Luo, Jin-Pei Cheng, Asymmetric Binary-Acid Catalysis with Chiral Phosphoric Acid and MgF2: Catalytic Enantioselective Friedel−Crafts Reactions of β,γ-Unsaturated α-Ketoesters Organic Letters. ,vol. 12, pp. 1096- 1099 ,(2010) , 10.1021/OL1000928
Yuhei Fukuta, Tsuyoshi Mita, Nobuhisa Fukuda, Motomu Kanai, Masakatsu Shibasaki, De novo synthesis of Tamiflu via a catalytic asymmetric ring-opening of meso-aziridines with TMSN3. Journal of the American Chemical Society. ,vol. 128, pp. 6312- 6313 ,(2006) , 10.1021/JA061696K
Emily B. Rowland, Gerald B. Rowland, Edwin Rivera-Otero, Jon C. Antilla, Brønsted Acid-Catalyzed Desymmetrization of meso-Aziridines Journal of the American Chemical Society. ,vol. 129, pp. 12084- 12085 ,(2007) , 10.1021/JA0751779
Giorgio Della Sala, Alessandra Lattanzi, Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of meso-Aziridines Organic Letters. ,vol. 11, pp. 3330- 3333 ,(2009) , 10.1021/OL901209N
Zhihui Shao, Hongbin Zhang, Combining transition metal catalysis and organocatalysis: a broad new concept for catalysis Chemical Society Reviews. ,vol. 38, pp. 2745- 2755 ,(2009) , 10.1039/B901258N
Shinji Murai, Noboru Sonoda, Noritaka Miyoshi, Hideo Ishii, Kiyoshi Kondo, CONVENIENT SYNTHESES OF PHENYL TRIMETHYLSILYL SELENIDE AND BENZENESELENOL Synthesis. ,vol. 1979, pp. 300- 301 ,(1979) , 10.1055/S-1979-28659
Biswanath Das, V. Saidi Reddy, R. Ramu, D. Nandan Kumar, A rapid regioselective ring-opening of aziridines with potassium thiocyanate using ammonium-12-molybdophosphate Catalysis Communications. ,vol. 7, pp. 997- 999 ,(2006) , 10.1016/J.CATCOM.2006.05.007
Martin Klussmann, Benjamin List, Lars Ratjen, Sebastian Hoffmann, Vijay Wakchaure, Richard Goddard, Synthesis of TRIP and Analysis of Phosphate Salt Impurities Synlett. ,vol. 2010, pp. 2189- 2192 ,(2010) , 10.1055/S-0030-1258505