Enantioselective synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives via an organocatalytic asymmetric Michael/cyclization cascade reaction
作者： Jin Xie , Xiao-Yu Xing , Feng Sha , Zhi-Yan Wu , Xin-Yan Wu
DOI: 10.1039/C6OB01256F
关键词:
摘要: An efficient enantioselective synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives by a cascade reaction between pyrazolones and isatylidene malononitriles is described. With only 1 mol% (DHQD)2PYR, chiral spirooxindole have been produced in excellent yields (96–99%) with good-to-excellent enantioselectivities (up to 91% ee).
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sci-hub.se 参考文章(66)
Fangrui Zhong, Xiaoyu Han, Youqing Wang, Yixin Lu, Highly enantioselective [4 + 2] annulations catalyzed by amino acid-based phosphines: Synthesis of functionalized cyclohexenes and 3-spirocyclohexene-2-oxindoles Chemical Science. ,vol. 3, pp. 1231- 1234 ,(2012) , 10.1039/C2SC00963C
Tian-Ze Li, Jin Xie, Yu Jiang, Feng Sha, Xin-Yan Wu, Enantioselective Vinylogous Michael/Cyclization Cascade Reaction of Acyclic β,γ‐Unsaturated Amides with Isatylidene Malononitriles: Asymmetric Construction of Spirocyclic Oxindoles Advanced Synthesis & Catalysis. ,vol. 357, pp. 3507- 3511 ,(2015) , 10.1002/ADSC.201500469
Fernando Auria-Luna, Eugenia Marqués-López, Somayeh Mohammadi, Roghayeh Heiran, Raquel Herrera, New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4'- (1',4'-dihydropyridine)] Derivatives. Molecules. ,vol. 20, pp. 15807- 15826 ,(2015) , 10.3390/MOLECULES200915807
Jin-Sheng Yu, Fu-Min Liao, Wei-Ming Gao, Kui Liao, Run-Lin Zuo, Jian Zhou, Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters Angewandte Chemie. ,vol. 54, pp. 7381- 7385 ,(2015) , 10.1002/ANIE.201501747
Daojuan Cheng, Yoshihiro Ishihara, Bin Tan, Carlos F. Barbas, Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies ACS Catalysis. ,vol. 4, pp. 743- 762 ,(2014) , 10.1021/CS401172R
Sai Yang, Liu-lan Shen, Yoon-Jung Kim, Jin-Hyun Jeong, Effective and novel enantioselective preparation of pyranopyrazoles and pyranocoumarins that is catalyzed by a quinine-derived primary amine. Organic and Biomolecular Chemistry. ,vol. 14, pp. 623- 630 ,(2016) , 10.1039/C5OB01656H
Nicolas R. Ball-Jones, Joseph J. Badillo, Annaliese K. Franz, Strategies for the enantioselective synthesis of spirooxindoles. Organic and Biomolecular Chemistry. ,vol. 10, pp. 5165- 5181 ,(2012) , 10.1039/C2OB25184A
Benedek Vakulya, Szilárd Varga, Antal Csámpai, Tibor Soós, Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts. Organic Letters. ,vol. 7, pp. 1967- 1969 ,(2005) , 10.1021/OL050431S
Ahmed A. Fadda, Ahmed El-Mekabaty, Khaled M. Elattar, Chemistry of Enaminonitriles of Pyrano[2,3-c]pyrazole and Related Compounds Synthetic Communications. ,vol. 43, pp. 2685- 2719 ,(2013) , 10.1080/00397911.2012.744842
Hua Zhao, Yu-Bao Lan, Zhao-Min Liu, Yong Wang, Xing-Wang Wang, Jing-Chao Tao, Enantioselective Construction of Spiro[2H-pyran-3,4′-indoline] by a Systematic Michael/Reduction/Cyclization Sequence Triggered by the Asymmetric Conjugate Addition of Ketones to Isatylidenemalononitriles European Journal of Organic Chemistry. ,vol. 2012, pp. 1935- 1944 ,(2012) , 10.1002/EJOC.201101810