Citation: Duan Cong, Ye Ling, Xu Wenqin, Li Xinying, Chen Feng, Zhao Zhigang, Li Xuefeng. Organocatalytic cascade 1, 6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes[J]. Chinese Chemical Letters, ;2018, 29(8): 1273-1276. doi: 10.1016/j.cclet.2017.11.044 shu

Organocatalytic cascade 1, 6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes

Duan Cong ^a ,
Ye Ling ^b ,
Xu Wenqin ^a ,
Li Xinying ^a ,
Chen Feng ^a ,
Zhao Zhigang ^a ,
Li Xuefeng ^a,,

a.
College of Chemistry and Environment Protection Engineering, Southwest Minzu University, Chengdu 610041, China
b.
Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University, Chengdu 610031, China

Corresponding author: Li Xuefeng, lixuefeng@swun.edu.cn
Received Date: 10 September 2017
Revised Date: 7 November 2017
Accepted Date: 30 November 2017
Available Online: 5 August 2017

Figures(3)

A novel organocatalytic cascade process initiated by 1, 6-conjugated addition has been successfully developed. A range of pharmaceutically active 2-amino-4-aryl-4H-chromenes were readily obtained in high yields (88%-99%) and excellent enantiopurities (86%-99% ee). The functionalized para-Quinone methides (p-OMs) could be facilely obtained.
- para-Quinone methides,
- 2-Amino-4-aryl-4H-chromene,
- Domino reaction,
- 1, 6-Conjugated addition,
- Enantioselective
1. [1]
  (a) S. A. Patil, R. Patil, L. M. Pfeffer, et al., Future Med. Chem. 5 (2013) 1647-1660;
  (b) J. L. Wang, D. Liu, Z. J. Zhang, et al., Proc. Natl. Acad. Sci. U. S. A. 97 (2000) 7124-7129.
2. [2]
  (a) S. Kasibhatla, H. Gourdeau, K. Meerovitch, et al., Mol. Cancer Ther. 3 (2004) 1365-1374;
  (b) S. X. Cai, J. Drewe, W. Kemnitzer, Anticancer Agents Med. Chem. 9 (2009) 437-456.
3. [3]
  W. Kemnitzer, J. Drewe, S. Jiang, et al., J. Med. Chem. 47 (2004) 6299-6310. doi: 10.1021/jm049640t
4. [4]
  H. Gourdeau, L. Leblond, B. Hamelin, et al., Mol. Cancer Ther. 3 (2004) 1375-1384.
5. [5]
  S.X. Cai, Recent Pat. Anticancer Drug Discov. 2 (2007) 79-101.
6. [6]
  S.X. Cai, J.A., Drewe, S. Kasibhatla, et al., U.S. Patent, 7, 968, 595 B2 (2011).
7. [7]
  (a) J. W. Xie, X. Huang, L. P. Fan, et al., Adv. Synth. Catal. 351 (2009) 3077-3082;
  (b) Y. Gao, W. Yang, D. M. Du, Tetrahedron: Asymmetry 23 (2012) 339-344;
  (c) G. Yang, C. Luo, X. Mu, et al., Chem. Commun. 48 (2012) 5880-5882;
  (d) W. Li, H. Liu, X. Jiang, et al., ACS Catal. 2 (2012) 1535-1538;
  (e) K. Hu, A. Lu, Y. Wang, et al., Tetrahedron: Asymmetry 24 (2013) 953-957;
  (f) W. Li, J. Huang, J. Wang, Org. Biomol. Chem. 11 (2013) 400-406;
  (g) Y. Q. Zheng, C. F. Luan, Z. J. Wang, et al., Chin. Chem. Lett. 27 (2016) 25-30;
  (h) A. Adili, Z. L. Tao, D. F. Chen, et al., Org. Biomol. Chem. 13 (2015) 2247-2250;
  (i) X. S. Wang, G. S. Yang, G. Zhao, Tetrahedron: Asymmetry 19 (2008) 709-714;
  (j) W. Chen, Y. Cai, X. Fu, et al., Org. Lett. 13 (2011) 4910-4913;
  (k) Y. Gao, D. M. Du, Tetrahedron: Asymmetry 24 (2013) 1312-1317;
  (l) B. Wu, X. Gao, Z. Yan, et al., Tetrahedron Lett. 56 (2015) 4334-4338;
  (m) B. Wu, X. Gao, Z. Yan, et al., Org. Lett. 17 (2015) 6134-6137;
  (n) L. Caruana, M. Mondatori, V. Corti, et al., Chem. -Eur. J. 21 (2015) 6037-6041;
  (o) Q. Ren, W. Y. Siau, Z. Du, et al., Chem. -Eur. J. 17 (2011) 7781-7785.
8. [8]
  (a) A. Parra, M. Tortosa, ChemCatChem 7 (2015) 1524-1526;
  (b) L. Caruana, M. Fochi, L. Bernardi, Molecules 20 (2015) 11733;
  (c) P. Chauhan, U. Kaya, D. Enders, Adv. Synth. Catal. 359 (2017) 888-912.
9. [9]
  (a) W. D. Chu, L. F. Zhang, X. Bao, et al., Angew. Chem. Int. Ed. 52 (2013) 9229-9233;
  (b) L. Caruana, F. Kniep, T. K. Johansen, et al., J. Am Chem. Soc. 136 (2014) 15929-15932;
  (c) Z. Wang, Y. F. Wong, J. Sun, Angew. Chem. Int. Ed. 54 (2015) 13711-13714;
  (d) Y. Lou, P. Cao, T. Jia, et al., Angew. Chem. Int. Ed. 54 (2015) 12134-12138;
  (e) F. S. He, J. H. Jin, Z. T. Yang, et al., ACS Catal. 6 (2016) 652-656;
  (f) K. Zhao, Y. Zhi, A. Wang, et al., ACS Catal. 6 (2016) 657-660;
  (g) X. Z. Zhang, Y. H. Deng, X. Yan, et al., J. Org. Chem. 81 (2016) 5655-5662;
  (i) X. Li, X. Xu, W. Wei, et al., Org. Lett. 18 (2016) 428-431;
  (j) Y. F. Wong, Z. Wang, J. Sun, Org. Biomol. Chem. 14 (2016) 5751-5754;
  (k) C. Ma, Y. Huang, Y. Zhao, ACS Catal. 6 (2016) 6408-6412;
  (l) L. Ge, X. Lu, C. Cheng, et al., J. Org Chem. 81 (2016) 9315-9325;
  (m) C. Jarava-Barrera, A. Parra, A. López, et al., ACS Catal. 6 (2016) 442-446;
  (n) N. Dong, Z. P. Zhang, X. S. Xue, et al., Angew. Chem. Int. Ed. 55 (2016) 1460-1464;
  (o) T. C. Kang, L. P. Wu, Q. W. Yu, et al., Chem. -Eur. J. 23 (2017) 6509-6513;
  (p) L. Roiser, M. Waser, Org. Lett. 19 (2017) 2338-2341;
  (q) S. Li, Y. Liu, B. Huang, et al., ACS Catal. 7 (2017) 2805-2809.
10. [10]
  (a) X. Z. Zhang, Y. H. Deng, K. J. Gan, et al., Org. Lett. 19 (2017) 1752-1755;
  (b) X. Z. Zhang, K. J. Gan, X. X. Liu, et al., Org. Lett. 19 (2017) 3207-3210.
11. [11]
  K. Zhao, Y. Zhi, T. Shu, et al., Angew. Chem. Int. Ed. 55 (2016) 12104-12108. doi: 10.1002/anie.201606947
12. [12]
  S. Liu, X.C. Lan, K. Chen, et al., Org. Lett. 19 (2017) 3831-3834. doi: 10.1021/acs.orglett.7b01705
13. [13]
  L. Zhang, X. Zhou, P. Li, et al., RSC Adv. 7 (2017) 39216-39220. doi: 10.1039/C7RA08157J
14. [14]
  B.J. Li, L. Jiang, M. Liu, et al., Synlett (2005) 603-606.
15. [15]
  J.P. Malerich, K. Hagihara, V.H. Rawal, J. Am. Chem. Soc. 130 (2008) 14416-14417. doi: 10.1021/ja805693p
1. [1]
  Shuai Zhu , Mingjie Chen , Haichao Shen , Hanming Ding , Wenbo Li , Junliang Zhang . Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature. Chinese Chemical Letters, 2024, 35(11): 109879-. doi: 10.1016/j.cclet.2024.109879
2. [2]
  Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp³)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
3. [3]
  Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
4. [4]
  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
5. [5]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
6. [6]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
7. [7]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
8. [8]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
9. [9]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
10. [10]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
11. [11]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
12. [12]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
13. [13]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
14. [14]
  Minghui Zhang , Na Zhang , Qian Zhao , Chao Wang , Alexander Steiner , Jianliang Xiao , Weijun Tang . Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines. Chinese Chemical Letters, 2025, 36(4): 110081-. doi: 10.1016/j.cclet.2024.110081
15. [15]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
16. [16]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
17. [17]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
18. [18]
  Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
19. [19]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
20. [20]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(743)
HTML views(2)

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