Synthesis of densely functionalized α-methylene γ-butyrolactones via an organocatalytic one-pot allylic-alkylation–cyclization reaction

作者: Yong Yan , Da En , Zhe Zhuang , Yuan Guo , Wei-Wei Liao

DOI: 10.1016/J.TETLET.2013.11.067

关键词:

摘要: Abstract The tertiary amine-catalyzed one-pot allylic-alkylation–cyclization (AAC) reaction has been developed, which provided an efficient synthetic route for the preparation of densely functionalized α-methylene-γ-cyano-γ-butyrolactones with various substituents at β-position and γ-position.

参考文章(36)
C. J. Douglas, L. E. Overman, Catalytic asymmetric synthesis of all-carbon quaternary stereocenters Proceedings of the National Academy of Sciences of the United States of America. ,vol. 101, pp. 5363- 5367 ,(2004) , 10.1073/PNAS.0307113101
Michael North, Dmitry L. Usanov, Carl Young, Lewis acid catalyzed asymmetric cyanohydrin synthesis. Chemical Reviews. ,vol. 108, pp. 5146- 5226 ,(2008) , 10.1021/CR800255K
Tian-Yu Liu, Min Xie, Ying-Chun Chen, Organocatalytic asymmetric transformations of modified Morita–Baylis–Hillman adducts Chemical Society Reviews. ,vol. 41, pp. 4101- 4112 ,(2012) , 10.1039/C2CS35017C
T. Patrick Montgomery, Abbas Hassan, Boyoung Y. Park, Michael J. Krische, Enantioselective conversion of primary alcohols to α-exo-methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation. Journal of the American Chemical Society. ,vol. 134, pp. 11100- 11103 ,(2012) , 10.1021/JA303839H
Andreas Otto, Berhanu Abegaz, Burkhard Ziemer, Jürgen Liebscher, Stereoselective synthesis of 3-(ω-hydroxyalkyl)-2-pyrrolidinones from α-alkylidenelactones and nitromethane Tetrahedron-asymmetry. ,vol. 10, pp. 3381- 3389 ,(1999) , 10.1016/S0957-4166(99)00346-8
Xavier Companyó, Andrea Mazzanti, Albert Moyano, Anna Janecka, Ramon Rios, First one-pot organocatalytic synthesis of α-methylene-γ-lactones Chemical Communications. ,vol. 49, pp. 1184- 1186 ,(2013) , 10.1039/C2CC38659C
Marco Bella, Tecla Gasperi, Organocatalytic formation of quaternary stereocenters Synthesis. ,vol. 2009, pp. 1583- 1614 ,(2009) , 10.1055/S-0029-1216796
Jean-Michel Brunel, Ian P. Holmes, Chemically Catalyzed Asymmetric Cyanohydrin Syntheses Angewandte Chemie International Edition. ,vol. 43, pp. 2752- 2778 ,(2004) , 10.1002/ANIE.200300604