Chiral squaramide as multiple H-bond donor organocatalysts for the asymmetric Michael addition of 1,3-dicarbonyl compounds to nitroolefins

作者: Ze Dong , Guofu Qiu , Hai-Bing Zhou , Chune Dong

DOI: 10.1016/J.TETASY.2012.10.016

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摘要: Abstract A series of chiral bifunctional squaramide multiple H-bond donor organocatalysts have been designed and synthesized by the rational assembly privileged scaffolds indanol cinchona alkaloids. In presence 1 mol % 1a , asymmetric Michael addition reaction 1,3-dicarbonyl compounds to nitroolefins proceeded provide product in high yields (up 92%) with good ee values 96%). The additional this system plays a crucial role enhancing enantioselectivity.

参考文章(50)
A. N. Thadani, A. R. Stankovic, V. H. Rawal, Enantioselective Diels–Alder reactions catalyzed by hydrogen bonding Proceedings of the National Academy of Sciences of the United States of America. ,vol. 101, pp. 5846- 5850 ,(2004) , 10.1073/PNAS.0308545101
Abigail G. Doyle, Eric N. Jacobsen, Small-molecule H-bond donors in asymmetric catalysis. Chemical Reviews. ,vol. 107, pp. 5713- 5743 ,(2007) , 10.1021/CR068373R
Xiang-Fei Wu, Chang Min, Enkhtsetseg Nyamzundui, Hai-Bing Zhou, Chune Dong, A novel C3-symmetric prolinol-squaramide catalyst for the asymmetric reduction of ketones by borane Tetrahedron-asymmetry. ,vol. 22, pp. 1640- 1643 ,(2011) , 10.1016/J.TETASY.2011.09.020
Lixin Li, Wenchao Chen, Wenguo Yang, Yuanhang Pan, Hongjun Liu, Choon-Hong Tan, Zhiyong Jiang, Bicyclic guanidine-catalyzed asymmetric Michael additions of 3-benzyl-substituted oxindoles to N-maleimides Chemical Communications. ,vol. 48, pp. 5124- 5126 ,(2012) , 10.1039/C2CC31587D
Christopher Uyeda, Eric N. Jacobsen, Enantioselective Claisen Rearrangements with a Hydrogen-Bond Donor Catalyst Journal of the American Chemical Society. ,vol. 130, pp. 9228- 9229 ,(2008) , 10.1021/JA803370X
Tomotaka Okino, Yasutaka Hoashi, Yoshiji Takemoto, Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts Journal of the American Chemical Society. ,vol. 125, pp. 12672- 12673 ,(2003) , 10.1021/JA036972Z
Andrew P. Dove, Russell C. Pratt, Bas G. G. Lohmeijer, Robert M. Waymouth, James L. Hedrick, Thiourea-Based Bifunctional Organocatalysis:  Supramolecular Recognition for Living Polymerization Journal of the American Chemical Society. ,vol. 127, pp. 13798- 13799 ,(2005) , 10.1021/JA0543346
Takahiko Akiyama, Junji Itoh, Koji Yokota, Kohei Fuchibe, Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid Angewandte Chemie. ,vol. 43, pp. 1566- 1568 ,(2004) , 10.1002/ANIE.200353240
Adam R. Brown, Wen-Hsin Kuo, Eric N. Jacobsen, Enantioselective Catalytic α-Alkylation of Aldehydes via an SN1 Pathway Journal of the American Chemical Society. ,vol. 132, pp. 9286- 9288 ,(2010) , 10.1021/JA103618R