Chiral Dawson-Type Hybrid Polyoxometalate Catalyzes Enantioselective Diels-Alder Reactions

作者: Wen-Jing Xuan , Candice Botuha , Bernold Hasenknopf , Serge Thorimbert

DOI: 10.1002/CHEM.201502839

关键词:

摘要: Can achiral organocatalysts linked to chiral polyanionic metal-oxide clusters provide good selectivity in enantioselective CC bond formations? We herein answer this question by disclosing a new active hybrid polyoxometalate-based catalyst for asymmetric Diels-Alder reaction. Chirality transfer from the anionic polyoxometalate covalently imidazolidinone allows us obtain cycloaddition products with yields and high enantioselectivities using cyclopentadiene acrylaldehydes as partners.

参考文章(84)
Bernold, Hasenknopf, Polyoxometalates: introduction to a class of inorganic compounds and their biomedical applications. Frontiers in Bioscience. ,vol. 10, pp. 275- 287 ,(2005) , 10.2741/1527
J. F. Austin, S.-G. Kim, C. J. Sinz, W.-J. Xiao, D. W. C. MacMillan, Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: synthesis of (-)-flustramine B. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 101, pp. 5482- 5487 ,(2004) , 10.1073/PNAS.0308177101
Wei-Lin Chen, Hua-Qiao Tan, En-Bo Wang, Review: The chirality and bionic studies of polyoxometalates: the synthetic strategy and structural chemistry Journal of Coordination Chemistry. ,vol. 65, pp. 1- 18 ,(2012) , 10.1080/00958972.2011.645812
Paolo Melchiorre, Mauro Marigo, Armando Carlone, Giuseppe Bartoli, Die asymmetrische Aminokatalyse – Goldrausch in der organischen Chemie Angewandte Chemie. ,vol. 120, pp. 6232- 6265 ,(2008) , 10.1002/ANGE.200705523
T. Mallat, E. Orglmeister, A. Baiker, Asymmetric catalysis at chiral metal surfaces. Chemical Reviews. ,vol. 107, pp. 4863- 4890 ,(2007) , 10.1021/CR0683663
Ya-Qian Lan, Shun-Li Li, Xin-Long Wang, Kui-Zhan Shao, Dong-Ying Du, Zhong-Min Su, En-Bo Wang, Spontaneous resolution of chiral polyoxometalate-based compounds consisting of 3D chiral inorganic skeletons assembled from different helical units. Chemistry: A European Journal. ,vol. 14, pp. 9999- 10006 ,(2008) , 10.1002/CHEM.200800666
Timothy J. Peelen, Yonggui Chi, Samuel H. Gellman, Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: cocatalyst effects and evidence for an enamine intermediate. Journal of the American Chemical Society. ,vol. 127, pp. 11598- 11599 ,(2005) , 10.1021/JA0532584
Claire Jahier, Sylvain Nlate, L‐Proline‐Derived Dendritic Tetrakis(diperoxotungsto)phosphate: Synthesis and Enantioselective Oxidation Catalysis European Journal of Inorganic Chemistry. ,vol. 2012, pp. 833- 840 ,(2012) , 10.1002/EJIC.201101145