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Citation: Min Zhang, Miao Li, Ting Qin, Zhiming Chen. Tandem Reaction of Ylide and Unsaturated Azlactone Catalyzed by C₂-axis Chiral Biguanide[J]. Chemistry, ;2021, 84(5): 480-485. shu

Tandem Reaction of Ylide and Unsaturated Azlactone Catalyzed by C₂-axis Chiral Biguanide

College of Chemistry and Materials Science, Guizhou Normal University, Guizhou Provincial Key Laboratory of Functional Materials Chemistry, Guiyang, 550001

Corresponding author: Zhiming Chen, czm000219@163.com
Received Date: 13 October 2020
Accepted Date: 20 December 2020

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In this paper, four chiral biguanide-amide catalysts based on the BINOL framework were successfully synthesized and applied to the 1, 3-dipolar cycloaddition and intramolecular tandem reaction of o-hydroxybenzaldehyde ylide and unsaturated azlactone. Using CHCl₃ as the solvent and axial chiral guanidine (1b, 10(mol)%) as the catalyst, reacting at room temperature for 12 hours, a series of benzopyran derivatives can be obtained with good yield (73%~88%) and high enantioselectivity (72%~86%).
- Axial chiral guanidine,
- 1, 3-Dipole ring addition,
- Intramolecular tandem reaction
1. [1]
  Emonds-Alt X, Grossriether I, Gueule P, et al. The law relating to financial crime in the United Kingdom, 2013.
2. [2]
  Khan M M, Shareef S, Saigal, et al. RSC Adv., 2019, 9(45): 26393~26401.
3. [3]
4. [4]
  Yang J, Qiu G, Jiang J, et al. Adv. Synth. Catal., 2017, 359(13): 2184~2190.
5. [5]
  Mazumder A, Wang S, Neamati N, et al. Med. Chem., 1996, 39: 472~475.
6. [6]
  Hiyama T, Oishi H, Suetsugu Y, et al. Bull. Chem. Soc. JPN, 1987, 60(6): 2139~2150.
7. [7]
  Narayanan D P, Balasubramanyan S, CherikallinmelS K, et al. ChemistrySelect, 2019, 4(16): 4785~4796.
8. [8]
  Irwin S, Prideaux B, Lyon E, et al. ACS Infect. Dis., 2016, 2(4): 251~267.
9. [9]
  Chen X H, Xu X Y, Liu H, et al. J. Am. Chem. Soc, 2006, 128(46): 14802~14803.
10. [10]
  Fylaktakidou K C, Hadjipavloulitina D, Litinas K E, et al. Curr. Pharm. Des., 2004, 10(30): 3813~3833.
11. [11]
  Sui Y P, Huo H R, Xin J J, et al. Molecules, 2015;20(9): 17614~17626.
12. [12]
  Shanthi G, Perumal P T. Tetrah. Lett., 2007, 48(38): 6785~6789.
13. [13]
  Zhou J, Wakchaure V N, Kraft P, et al. Angew. Chem. Int. Ed., 2008, 47(40): 7656~7658.
14. [14]
  Yang J, Qiu G, Jiang J, et al. Adv. Synth. Catal., 2017, 359(13): 2184~2190.
15. [15]
  Rapposelli S, Settimo F D, Digiacomo M, et al. Archiv. Der. Pharm., 2011, 344(6): 372~385.
16. [16]
17. [17]
18. [18]
  Bastida D, Liu Y, Tian X, et al. Org. Lett., 2012, 15(1): 220~223.
19. [19]
  Spatola A F, Anwer M K, Rockwell A L, et al. J. Am. Chem. Soc., 2002, 108(4): 825~831.
20. [20]
1. [1]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
2. [2]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
3. [3]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
4. [4]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
5. [5]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
6. [6]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
7. [7]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
8. [8]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
9. [9]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
10. [10]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
11. [11]
  Guilan He , Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122
12. [12]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
13. [13]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
14. [14]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
15. [15]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
16. [16]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
17. [17]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
18. [18]
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19. [19]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
20. [20]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046

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Tandem Reaction of Ylide and Unsaturated Azlactone Catalyzed by C2-axis Chiral Biguanide

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通讯作者: 陈斌, bchen63@163.com

Tandem Reaction of Ylide and Unsaturated Azlactone Catalyzed by C₂-axis Chiral Biguanide