Citation: Ma Rong, Song Gege, Xi Qiuzhen, Yang Liu, Li Er-Qing, Duan Zheng. Phosphine-Catalyzed[3+2] Annulations with γ-Methyl Allenoates[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2196-2202. doi: 10.6023/cjoc201901040 shu

Phosphine-Catalyzed[3+2] Annulations with γ-Methyl Allenoates

International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Corresponding author: Li Er-Qing, lierqing@zzu.edu.cn Duan Zheng, duanzheng@zzu.edu.cn
Received Date: 25 January 2019
Revised Date: 22 March 2019
Available Online: 9 August 2019
Fund Project: the National Natural Science Foundation of China 21272218the National Natural Science Foundation of China 21702189the China Postdoctoral Science Foundation 2018T110737the Postdoctoral Research Grant in Henan Province 001701006Project supported by the National Natural Science Foundation of China (Nos. 21702189, 21672193, 21272218), the China Postdoctoral Science Foundation (Nos. 2017M610458, 2018T110737) and the Postdoctoral Research Grant in Henan Province (No. 001701006)the National Natural Science Foundation of China 21672193the China Postdoctoral Science Foundation 2017M610458

Figures(2)

The phosphine-catalyzed[3+2] annulation of γ-methyl allenoates with 2-arylidene-1H-indene-1, 3(2H)-diones is reported. In the reaction, a series of highly functionalized spiro[4.4]dec-6-ene skeletons were obtained in moderate to good yields and high diastereoselectivities. It should be noted that the perfect α-regioselective annulation adducts were obtained with simple PPh₃ catalyst.
- phosphine-catalyzed,
- γ-methyl allenoates,
- [3+2]annulation
1. [1]
  (a) Tan, B.; Candeias, N. R.; Barbas Ⅲ, C. F. Nat. Chem. 2011, 3, 473.
  (b) Tan, B.; Candeias, N. R.; Barbas Ⅲ, C. F. J. Am. Chem. Soc. 2011, 133, 4672.
  (c) Tan, B.; Hernandez-Torres, G.; Barbas Ⅲ, C. F. J. Am. Chem. Soc. 2011, 133, 12354.
  (d) Cao, Y.; Jiang, X.; Liu, L.; Shen, F.; Zhang, F.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 9124.
  (e) Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2011, 50, 7837.
  (f) Bencivenni, G.; Wu, L.-Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M.-P.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7200.
2. [2]
  (a) Hojo, D.; Noguchi, K.; Tanaka, K. Angew. Chem., Int. Ed. 2009, 48, 8129.
  (b) Tanaka, K.; Otake, Y.; Sagae, H.; Noguchi, K.; Hirano, M. Angew. Chem., Int. Ed. 2008, 47, 1312.
  (c) Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396.
3. [3]
  (a) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
  (b) Lu, Z.; Zheng, S.; Zhang, X.; Lu, X. Org. Lett. 2008, 10, 3267.
  (c) Zhang, B.; He, Z.; Xu, S.; Wu, G.; He, Z. Tetrahedron 2008, 64, 9471.
  (d) Tian, J.; He, Z. Chem. Commun. 2013, 49, 2058.
4. [4]
5. [5]
  (a) Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
  (b) Tran, Y. S.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 12632.
  (c) Chen, R.; Fan, X.; Xu, Z.; He, Z. Chin. J. Chem. 2017, 35, 1469.
6. [6]
  Zhang, Q.; Yang, L.; Tong, X. J. Am. Chem. Soc. 2010, 132, 2550. doi: 10.1021/ja100432m
7. [7]
  (a) Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Chem.-Eur. J. 2009, 15, 8698.
  (b) Meng, X.; Huang, Y.; Zhao, H.; Xie, P.; Ma, J.; Chen, R. Org. Lett. 2009, 11, 991.
  (c) Zhao, H.; Meng, X.; Huang, Y. Chem. Commun. 2013, 49, 10513.
  (d) Li, E.; Jia, P.; Liang, L.; Huang, Y. ACS Catal. 2014, 4, 600.
  (e) Li, E.; Chang, M.; Liang, L.; Huang, Y. Eur. J. Org. Chem. 2015, 710.
  (f) Li, E.; Jin, H.; Huang, Y. ChemistrySelect 2018, 3, 12007.
8. [8]
  Zhang, X.-C.; Cao, S.-H.; Wei, Y.; Shi, M. Chem. Commun. 2011, 47, 1548. doi: 10.1039/C0CC04289G
9. [9]
  Gomez, C.; Gicquel, M.; Carry, J.-C.; Schio, L.; Retailleau, P.; Voituriez, A.; Marinetti, A. J. Org. Chem. 2013, 78, 1488. doi: 10.1021/jo302460d
10. [10]
  Li, E.; Huang, Y.; Liang, L.; Xie, P. Org. Lett. 2013, 15, 3138. doi: 10.1021/ol401249e
11. [11]
  CCDC 1579810 (3e) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
12. [12]
  (a) Liang, Y.; Liu, S.; Xia, Y.; Li, Y.; Yu, Z.-X. Chem.-Eur. J. 2008, 14, 4361.
  (b) Mercier, E.; Fonovic, B.; Henry, C.; Kwon, O.; Dudding, T. Tetrahedron Lett. 2007, 48, 3617.
  (c) Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 3470.
  (d) Dudding, T.; Kwon, O.; Mercier, E. Org. Lett. 2006, 8, 3643.
  (e) Zhu, X.-F.; Henry, C. E.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 6722.
13. [13]
  Goswami, P.; Das, B. Tetrahedron Lett. 2009, 50, 897. doi: 10.1016/j.tetlet.2008.12.036
14. [14]
  Lang, R. W.; Hansen, H.-J. Org. Synth. 1990, 62, 202.
1. [1]
  Junyuan Zhang , Zhiwei Miao . 有机磷杀虫剂的前世今生. University Chemistry, 2025, 40(6): 129-138. doi: 10.12461/PKU.DXHX202408118
2. [2]
  Yachao HUANG , Chuanwang ZENG , Guiyong LIU , Jinming ZENG , Chao LIU , Xiaopeng QI . Oxygen vacancies and phosphorus doping enhanced metal-organic framework derived nitrogen-doped carbon-coated Co₃O₄ bifunctional electrocatalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2251-2260. doi: 10.11862/CJIC.20250133
3. [3]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
4. [4]
  Ruige ZHANG , Zhe ZHANG , He ZHENG , Zhan SHI . Recent advances of metal-organic frameworks for alkaline electrocatalytic oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2011-2028. doi: 10.11862/CJIC.20250185
5. [5]
  Qilong Fang , Yiqi Li , Jiangyihui Sheng , Quan Yuan , Jie Tan . Magical Pesticide Residue Detection Test Strips: Aptamer-based Lateral Flow Test Strips for Organophosphorus Pesticide Detection. University Chemistry, 2024, 39(5): 80-89. doi: 10.3866/PKU.DXHX202310004
6. [6]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
7. [7]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
8. [8]
  Fengxiao Wang , Zhiwei Miao , Yaofeng Yuan . 有机磷化学与化学教学. University Chemistry, 2025, 40(8): 158-168. doi: 10.12461/PKU.DXHX202410077
9. [9]
  Wen WANG , Ying XU , Gang XIONG , Lixin YOU , Yaguang SUN . Pd-NHC-functionalized La-metal-organic framework for efficient Suzuki-Miyaura cross-coupling reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1475-1484. doi: 10.11862/CJIC.20260025
10. [10]
  Guoqiang Peng , Xiuyan Li , Min Li , Zhibo Su , Falu Hu , Guowei Zhou . Engineering efficient metal-organic frameworks for photocatalytic CO₂ reduction. Acta Physico-Chimica Sinica, 2026, 42(2): 100164-0. doi: 10.1016/j.actphy.2025.100164
11. [11]
  Hongjing ZHU , Guanying LIU , Kuaibing WANG . Application of in-situ characterization in electrocatalytic CO₂ reduction reaction of metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2026, 42(9): 1893-1909. doi: 10.11862/CJIC.20260144
12. [12]
  Wenjun Zhu , Chenbin Ai , Kaiqiang Xu , Yatai Zhou , Xidong Zhang , Yong Zhang . WO₃@TP inorganic@organic S-scheme photocatalyst for boosting H₂O₂ production. Acta Physico-Chimica Sinica, 2026, 42(3): 100184-0. doi: 10.1016/j.actphy.2025.100184
13. [13]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . Architecting Inorganic/Organic S-Scheme Heterojunction of Bi₄Ti₃O₁₂ Coupling with g-C₃N₄ for Photocatalytic H₂O₂ Production from Pure Water. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-0. doi: 10.3866/PKU.WHXB202403009
14. [14]
  Shuai Yuan , Yaofeng Yuan . Academician Chengye Yuan and Organic Phosphorus Chemistry. University Chemistry, 2025, 40(7): 393-400. doi: 10.12461/PKU.DXHX202409123
15. [15]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
16. [16]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
17. [17]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
18. [18]
  Shuang Cao , Bo Zhong , Chuanbiao Bie , Bei Cheng , Feiyan Xu . Insights into Photocatalytic Mechanism of H₂ Production Integrated with Organic Transformation over WO₃/Zn_0.5Cd_0.5S S-Scheme Heterojunction. Acta Physico-Chimica Sinica, 2024, 40(5): 2307016-0. doi: 10.3866/PKU.WHXB202307016
19. [19]
  Wenjuan SHI , Yuke LU , Xiuyuan LI , Lei HOU , Yaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO₂ adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220
20. [20]
  Xiaomin Kang , Chuanbao Jiao . Application of Metal-Organic Frameworks in CO₂ Catalytic Conversion: Promoting “Double Carbon” Actions for a Beautiful China. University Chemistry, 2026, 41(2): 208-217. doi: 10.12461/PKU.DXHX202503011

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(2722)
HTML views(328)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142