Palladium-catalyzed tandem allylic substitution/cyclization and cascade hydrosilylated reduction: the influence of reaction parameters and hydrosilanes on the stereoselectivity

作者: Peng-Wei Long , Jian-Xing Xu , Xing-Feng Bai , Zheng Xu , Zhan-Jiang Zheng

DOI: 10.1039/C8RA02995D

关键词:

摘要: To shed light on the influence of reaction parameters palladium-catalyzed tandem allylic alkylation in presence Fei-Phos (a chiral trans-1,2-diaminocyclohexane-derived phosphine ligand), effect different ligands, inorganic or organic bases, Bronsted acids, and other additives asymmetric palladium-catalysed catechol with diacetate was investigated. In this reaction, 2-vinyl-2,3-dihydro-benzo[1,4]dioxin products promising enantioselectivity were achieved good yields. addition, a novel three-component one-pot substitution/cyclization/reduction assisted by methylphenylsilane reported selectivity.

参考文章(86)
Cheng Dong, Tao Song, Xing-Feng Bai, Yu-Ming Cui, Zheng Xu, Li-Wen Xu, Enantioselective conjugate addition of cyanide to chalcones catalyzed by a magnesium-Py-BINMOL complex Catalysis Science & Technology. ,vol. 5, pp. 4755- 4759 ,(2015) , 10.1039/C5CY01056J
Marc Magre, Maria Biosca, Per-Ola Norrby, Oscar Pàmies, Montserrat Diéguez, Theoretical and Experimental Optimization of a New Amino Phosphite Ligand Library for Asymmetric Palladium‐Catalyzed Allylic Substitution Chemcatchem. ,vol. 7, pp. 4091- 4107 ,(2015) , 10.1002/CCTC.201500873
Wen-Hui Deng, Fei Ye, Xing-Feng Bai, Zhan-Jiang Zheng, Yu-Ming Cui, Li-Wen Xu, Multistereogenic Phosphine Ligand‐promoted Palladium‐Catalyzed Allylic Alkylation of Cyanoesters Chemcatchem. ,vol. 7, pp. 75- 79 ,(2015) , 10.1002/CCTC.201402733
Gay P. Fagan, Christopher B. Chapleo, Anthony C. Lane, Malcolm Myers, Alan G. Roach, Colin F. C. Smith, Michael R. Stillings, Anthony P. Welbourn, Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists Journal of Medicinal Chemistry. ,vol. 31, pp. 944- 948 ,(1988) , 10.1021/JM00400A009
Long-Sheng Zheng, Li Li, Ke-Fang Yang, Zhan-Jiang Zheng, Xu-Qiong Xiao, Li-Wen Xu, New silver(I)–monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction Tetrahedron. ,vol. 69, pp. 8777- 8784 ,(2013) , 10.1016/J.TET.2013.07.105
Li Dai, Xin Li, Hao Yuan, Xia Li, Zhihuai Li, Di Xu, Fan Fei, Yingqiang Liu, Jun Zhang, Zhiming Zhou, Ionic-salt-tagged ferrocenyl diphosphine–imine ligands and their application to palladium-catalyzed asymmetric allylic etherification Tetrahedron-asymmetry. ,vol. 22, pp. 1379- 1389 ,(2011) , 10.1016/J.TETASY.2011.07.025
Barry M. Trost, New rules of selectivity: allylic alkylations catalyzed by palladium Accounts of Chemical Research. ,vol. 12, pp. 385- 393 ,(1980) , 10.1021/AR50155A001
Louise A. Evans, Natalie Fey, Jeremy N. Harvey, David Hose, Guy C. Lloyd-Jones, Paul Murray, A. Guy Orpen, Robert Osborne, Gareth J. J. Owen-Smith, Mark Purdie, Counterintuitive Kinetics in Tsuji-Trost Allylation: Ion-pair Partitioning and Implications for Asymmetric Catalysis Journal of the American Chemical Society. ,vol. 130, pp. 14471- 14473 ,(2008) , 10.1021/JA806278E
Ping Fang, Chang-Hua Ding, Xue-Long Hou, Li-Xin Dai, Palladium-catalyzed regio- and enantio-selective allylic substitution reaction of monosubstituted allyl substrates with benzyl alcohols Tetrahedron-asymmetry. ,vol. 21, pp. 1176- 1178 ,(2010) , 10.1016/J.TETASY.2010.03.045
Mercè Coll, Oscar Pàmies, Montserrat Diéguez, Highly versatile Pd-thioether-phosphite catalytic systems for asymmetric allylic alkylation, amination, and etherification reactions. Organic Letters. ,vol. 16, pp. 1892- 1895 ,(2014) , 10.1021/OL500758Y