Enantioselective Aldol Reaction using Recyclable Montmorillonite‐Entrapped N‐(2‐Thiophenesulfonyl)prolinamide

作者: Noriyuki Hara , Shuichi Nakamura , Norio Shibata , Takeshi Toru

DOI: 10.1002/ADSC.201000214

关键词:

摘要: N-(2-Thiophenesulfonyl)prolinamide could be easily introduced into Montmorillonite by a simple ion-exchange reaction. The asymmetric aldol reactions between various isatins with acetone or acetaldehyde using heterogeneous Montmorillonite-entrapped organocatalyst afforded products high enantioselectivity. catalyst was readily reusable without significant loss of catalytic activity

参考文章(19)
Santanu Mukherjee, Jung Woon Yang, Sebastian Hoffmann, Benjamin List, Asymmetric enamine catalysis. Chemical Reviews. ,vol. 107, pp. 5471- 5569 ,(2007) , 10.1021/CR0684016
Gabriela Guillena, Carmen Nájera, Diego J. Ramón, Enantioselective direct aldol reaction: the blossoming of modern organocatalysis Tetrahedron-asymmetry. ,vol. 18, pp. 2249- 2293 ,(2007) , 10.1016/J.TETASY.2007.09.025
Michelangelo Gruttadauria, Francesco Giacalone, Renato Noto, Supported proline and proline-derivatives as recyclable organocatalysts Chemical Society Reviews. ,vol. 37, pp. 1666- 1688 ,(2008) , 10.1039/B800704G
Yoshiaki Kamano, Hui-ping Zhang, Yoshitatsu Ichihara, Haruhisa Kizu, Kanki Komiyama, George R. Pettit, Convolutamydine A, a novel bioactive hydroxyoxindole alkaloid from marine bryozoan Amathia convoluta Tetrahedron Letters. ,vol. 36, pp. 2783- 2784 ,(1995) , 10.1016/0040-4039(95)00395-S
Teruhisa Tokunaga, W. Ewan Hume, Takashi Umezome, Kazuhiko Okazaki, Yasuyuki Ueki, Kazuo Kumagai, Shinji Hourai, Jun Nagamine, Hitoshi Seki, Mutsuo Taiji, Hiroshi Noguchi, Ryu Nagata, Oxindole derivatives as orally active potent growth hormone secretagogues. Journal of Medicinal Chemistry. ,vol. 44, pp. 4641- 4649 ,(2001) , 10.1021/JM0103763
Takato Mitsudome, Kenta Nose, Tomoo Mizugaki, Koichiro Jitsukawa, Kiyotomi Kaneda, Reusable montmorillonite-entrapped organocatalyst for asymmetric Diels–Alder reaction Tetrahedron Letters. ,vol. 49, pp. 5464- 5466 ,(2008) , 10.1016/J.TETLET.2008.07.011
Jie Liu, Zhigang Yang, Zhen Wang, Fei Wang, Xiaohong Chen, Xiaohua Liu, Xiaoming Feng, Zhishan Su, Changwei Hu, Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine. Journal of the American Chemical Society. ,vol. 130, pp. 5654- 5655 ,(2008) , 10.1021/JA800839W
Maurizio Benaglia, Alessandra Puglisi, Franco Cozzi, Polymer-Supported Organic Catalysts† Chemical Reviews. ,vol. 103, pp. 3401- 3429 ,(2003) , 10.1021/CR010440O
Štefan Toma, Mária Mečiarová, Radovan Šebesta, Are Ionic Liquids Suitable Media for Organocatalytic Reactions European Journal of Organic Chemistry. ,vol. 2009, pp. 321- 327 ,(2009) , 10.1002/EJOC.200800809
Shuichi Nakamura, Noriyuki Hara, Hiroki Nakashima, Koji Kubo, Norio Shibata, Takeshi Toru, Enantioselective Synthesis of (R)‐Convolutamydine A with New N‐Heteroarylsulfonylprolinamides Chemistry: A European Journal. ,vol. 14, pp. 8079- 8081 ,(2008) , 10.1002/CHEM.200800981