Diastereoselective three-component Mannich reaction catalyzed by silica-supported ferric hydrogensulfate

作者: Hossein Eshghi , Mohammad Rahimizadeh , Mohsen Hosseini , Aida Javadian-Saraf

DOI: 10.1007/S00706-012-0800-Y

关键词:

摘要: A highly anti-diastereoselective three-component Mannich reaction of aromatic amines and aldehydes with cyclohexanone in the presence silica-supported ferric hydrogensulfate has been developed. The best selectivity was obtained where there were electron-donating groups on both aldehyde amine. Selectivity decreases when electron-withdrawing are present aldehyde; these cases is improved if an group

参考文章(61)
Hossein Eshghi, Afsaneh Alipour, Saman Damavandi, Highly Efficient Fe(HSO4)3-Catalyzed One-Pot Mannich-Type Reactions: Three Component Synthesis of β-amino Carbonyl Compounds Synthesis and Reactivity in Inorganic Metal-organic and Nano-metal Chemistry. ,vol. 41, pp. 266- 271 ,(2011) , 10.1080/15533174.2011.555858
Jun Xia, Renhua Qiu, Shuangfeng Yin, Xiaowen Zhang, Shenglian Luo, Chak-Tong Au, Kai Xia, Wai-Yeung Wong, Synthesis and structure of an air-stable organoantimony complex and its use as a catalyst for direct diastereoselective Mannich reactions in water Journal of Organometallic Chemistry. ,vol. 695, pp. 1487- 1492 ,(2010) , 10.1016/J.JORGANCHEM.2010.03.003
Qi-Xiang Guo, Hua Liu, Chang Guo, Shi-Wei Luo, Yi Gu, Liu-Zhu Gong, Chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction. Journal of the American Chemical Society. ,vol. 129, pp. 3790- 3791 ,(2007) , 10.1021/JA068236B
Haile Zhang, Maria Mifsud, Fujie Tanaka, Carlos F. Barbas, 3-Pyrrolidinecarboxylic acid for direct catalytic asymmetric anti-Mannich-type reactions of unmodified ketones. Journal of the American Chemical Society. ,vol. 128, pp. 9630- 9631 ,(2006) , 10.1021/JA062950B
Mazaahir Kidwai, Neeraj Kumar Mishra, Vikas Bansal, Ajeet Kumar, Subho Mozumdar, Novel one-pot Cu-nanoparticles-catalyzed Mannich reaction Tetrahedron Letters. ,vol. 50, pp. 1355- 1358 ,(2009) , 10.1016/J.TETLET.2009.01.031
Benjamin List, The Direct Catalytic Asymmetric Three-Component Mannich Reaction Journal of the American Chemical Society. ,vol. 122, pp. 9336- 9337 ,(2000) , 10.1021/JA001923X
Hui Wu, Xiu-mei Chen, Yu Wan, Ling Ye, Hai-qiang Xin, Hua-hong Xu, Cai-hui Yue, Li-ling Pang, Rui Ma, Da-qing Shi, Stereoselective Mannich reactions catalyzed by Tröger’s base derivatives in aqueous media Tetrahedron Letters. ,vol. 50, pp. 1062- 1065 ,(2009) , 10.1016/J.TETLET.2008.12.067
Abbas Ali Jafari, Fatemeh Moradgholi, Fatemeh Tamaddon, Pronounced Catalytic Effect of a Micellar Solution of Sodium Dodecylsulfate (SDS) Upon a Three‐Component Reaction of Aldehydes, Amines, and Ketones Under Neutral Conditions European Journal of Organic Chemistry. ,vol. 2009, pp. 1249- 1255 ,(2009) , 10.1002/EJOC.200801037
Paul Ha-Yeon Cheong, Haile Zhang, Rajee Thayumanavan, Fujie Tanaka, K. N. Houk, Carlos F. Barbas, Pipecolic Acid-Catalyzed Direct Asymmetric Mannich Reactions Organic Letters. ,vol. 8, pp. 811- 814 ,(2006) , 10.1021/OL052861O
Xu-Feng Lin, Deng Hong, Yun-Yun Yang, Yan-Guang Wang, A Yb(OTf)3/PEG-SupportedQuaternary Ammonium Salt Catalyst System for a Three-Component Mannich-TypeReaction in Aqueous Media Synlett. ,vol. 2009, pp. 1107- 1110 ,(2009) , 10.1055/S-0028-1088221