Citation: Li Yao, Chen Kunquan, Zhang Yan, Sun Dequn, Ye Song. N-Heterocyclic carbene-catalyzed[4 + 2] cyclization of α-chloroaldehydes and aurones: Highly enantioselective synthesis of benzofuran-fused dihydropyran-2-ones[J]. Chinese Chemical Letters, ;2018, 29(8): 1209-1211. doi: 10.1016/j.cclet.2018.03.003 shu

N-Heterocyclic carbene-catalyzed[4 + 2] cyclization of α-chloroaldehydes and aurones: Highly enantioselective synthesis of benzofuran-fused dihydropyran-2-ones

Li Yao ^a,b,1 ,
Chen Kunquan ^b,c,1 ,
Zhang Yan ^b ,
Sun Dequn ^a,, ,
Ye Song ^b,c,,

a.
Marine College, Shandong University at Weihai, Weihai 264209, China
b.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Sun Dequn, dequn.sun@sdu.edu.cn Ye Song, songye@iccas.ac.cn

Received Date: 3 January 2018
Revised Date: 3 February 2018
Accepted Date: 1 March 2018
Available Online: 3 August 2018

Figures(4)

The chiral N-heterocyclic carbene-catalyzed[4 + 2] annulation of α-chloroaldehydes and aurones was developed, giving the corresponding benzofuran-fused dihydropyranones in good to high yields with good diastereoselectivities and excellent enantioselectivities. The catalytic cycle features with the generation of enolate from chloroaldehdye and its following[4 + 2] cycloaddtion with aurones.
- Carbene catalysis,
- Annulation,
- Enantioselectivity,
- Benzofuran,
- Dihydropranone
1. [1]
  R. Breslow, J. Am, Chem. Soc. 80(1958) 3719-3726. doi: 10.1021/ja01547a064
2. [2]
  D. Enders, U. Kallfass, Angew. Chem. Int. Ed. 41(2002) 1743-1745. doi: 10.1002/(ISSN)1521-3773
3. [3]
  M.S. Kerr, T. Rovis, J. Am. Chem. Soc. 126(2004) 8876-8877. doi: 10.1021/ja047644h
4. [4]
  H. Stetter, M. Schreckenberg, Angew. Chem. Int. Ed. 12(1973) 81-81.
5. [5]
  Q.F. Cheng, J.W. Wang, Q.F. Wang, Z. Liu, Chin. Chem. Lett. 27(2016) 1032-1035. doi: 10.1016/j.cclet.2016.03.007
6. [6]
  R.S. Menon, A.T. Biju, V. Nair, Chem. Soc. Rev. 44(2015) 5040-5052. doi: 10.1039/C5CS00162E
7. [7]
  N. Gaggero, S. Pandini, Org. Biomol. Chem. 15(2017) 6867-6887. doi: 10.1039/C7OB01662J
8. [8]
  Q. Ren, M.Y. Li, L.J. Yuan, J. Wang, Org. Biomol. Chem. 15(2017) 4731-4749. doi: 10.1039/C7OB00568G
9. [9]
  P. Shao, L. Shen, S. Ye, Chin. J. Chem. (2012) 2688-2692.
10. [10]
  L.A. Collett, M.T. Davies-Coleman, D.E.A. Rivett, Prog. Chem. Org. Nat. Prod. 75(1998) 181-209.
11. [11]
  X. Hao, L. Lin, F. Tan, et al., ACS Catal. 5(2015) 6052-6056. doi: 10.1021/acscatal.5b01719
12. [12]
  D.D. Borisov, R.A. Novikov, A.S. Eltysheva, Y.V. Tkachev, Y.V. Tomilov, Org. Lett. 19(2017) 3731-3734. doi: 10.1021/acs.orglett.7b01556
13. [13]
  J. Zhang, J.L. Wu, Chin. Chem. Lett. 27(2016) 1537-1540. doi: 10.1016/j.cclet.2016.03.034
14. [14]
  M. He, G.J. Uc, J.W. Bode, J. Am. Chem. Soc. 128(2006) 15088-15089. doi: 10.1021/ja066380r
15. [15]
  M. He, B.J. Beahm, J.W. Bode, Org. Lett. 10(2008) 3817-3820. doi: 10.1021/ol801502h
16. [16]
  S. Li, X.Y. Chen, Q. Liu, et al., Synthesis 49(2017) 4861-4868. doi: 10.1055/s-0036-1588509
17. [17]
  K.Q. Chen, H.M. Zhang, D.L. Wang, D.Q. Sun, S. Ye, Org. Biomol. Chem.13(2015) 6694-6697. doi: 10.1039/C5OB00859J
18. [18]
  A.T. Davies, J.E. Taylor, J. Douglas, et al., J. Org. Chem. 78(2013) 9243-9257. doi: 10.1021/jo401433q
19. [19]
  Y.R. Zhang, H. Lv, D. Zhou, S. Ye, Chem.-Eur. J. 14(2008) 8473-8476. doi: 10.1002/chem.v14:28
20. [20]
  H. Lv, X.Y. Chen, L.H. Sun, S. Ye, J. Org. Chem. 75(2010) 6973-6976. doi: 10.1021/jo101318u
21. [21]
  T.Y. Jian, X.Y. Chen, L.H. Sun, S. Ye, Org. Biomol. Chem. 11(2013) 158-163. doi: 10.1039/C2OB26804C
22. [22]
  J. Mo, R. Yang, X. Chen, B. Tiwari, Y.R. Chi, Org. Lett. 15(2013) 50-53. doi: 10.1021/ol303035r
23. [23]
  P.J.W. Fuchs, K. Zeitler, Org. Lett. 19(2017) 6076-6079. doi: 10.1021/acs.orglett.7b02889
24. [24]
  L. Prieto, E. Sanchez-Diez, U. Uria, et al., Adv. Synth. Catal. 359(2017) 1678-1683. doi: 10.1002/adsc.v359.10
25. [25]
  L.T. Shen, P.L. Shao, S. Ye, Adv. Synth. Catal. 353(2011) 1943-1948. doi: 10.1002/adsc.v353.11/12
26. [26]
  R. Liu, C. Yu, Z. Xiao, Org. Biomol. Chem. 12(2014) 1885-1891. doi: 10.1039/C3OB42008F
27. [27]
  S. De Sarkar, A. Studer, Angew. Chem. Int. Ed. 49(2010) 9266-9269. doi: 10.1002/anie.201004593
28. [28]
  A. Axelsson, E. Hammarvid, L. Ta, H. Sunden, Chem. Commun. 52(2016) 11571-11574. doi: 10.1039/C6CC06060A
29. [29]
  D. Xie, D. Shen, Q. Chen, et al., J. Org. Chem. 81(2016) 6136-6141. doi: 10.1021/acs.joc.6b01152
30. [30]
  F.G. Sun, L.H. Sun, S. Ye, Adv. Synth. Catal. 353(2011) 3134-3138. doi: 10.1002/adsc.v353.17
31. [31]
  G. Wang, X. Chen, G. Miao, W. Yao, C. Ma, J. Org. Chem. 78(2013) 6223-6232. doi: 10.1021/jo400950j
32. [32]
  C. Yao, D. Wang, J. Lu, Chem.-Eur. J. 18(2012) 1914-1917. doi: 10.1002/chem.201103358
33. [33]
  C. Yao, Z. Xiao, R. Liu, et al., Chem.-Eur. J. 19(2013) 456-459. doi: 10.1002/chem.201202655
34. [34]
  S.R. Yetra, A. Bhunia, A. Patra, et al., Adv. Synth. Catal. 355(2013) 1089-1097. doi: 10.1002/adsc.v355.6
35. [35]
  Z. Xiao, C. Yu, T. Li, X.S. Wang, C. Yao, Org. Lett. 16(2014) 3632-3635. doi: 10.1021/ol501224p
36. [36]
  S.R. Yetra, T. Kaicharla, S.S. Kunte, R.G. Gonnade, A.T. Biju, Org. Lett. 15(2013) 5202-5205. doi: 10.1021/ol4026155
37. [37]
  J. Kaeobamrung, J. Mahatthananchai, P. Zheng, J.W. Bode, J. Am. Chem. Soc.132(2010) 8810-8812. doi: 10.1021/ja103631u
38. [38]
  Z.Q. Zhu, J.C. Xiao, Adv. Synth. Catal. 352(2010) 2455-2458. doi: 10.1002/adsc.v352:14/15
39. [39]
  J. Mahatthananchai, J. Kaeobamrung, J.W. Bode, ACS Catal. 2(2012) 494-503. doi: 10.1021/cs300020t
40. [40]
  S.J. Ryan, L. Candish, D.W. Lupton, J. Am. Chem. Soc. 131(2009) 14176-14177. doi: 10.1021/ja905501z
41. [41]
  L. Candish, D.W. Lupton, Org. Lett. 12(2010) 4836-4839. doi: 10.1021/ol101983h
42. [42]
  Q. Ni, J. Xiong, X. Song, G. Raabe, D. Enders, Chem. Commun. 51(2015) 14628-14631. doi: 10.1039/C5CC06044C
43. [43]
  Y. Que, T. Li, C. Yu, X.S. Wang, C. Yao, J. Org. Chem. 80(2015) 3289-3294. doi: 10.1021/jo502920w
44. [44]
  L. Candish, D.W. Lupton, Chem. Sci. 3(2012) 380-383. doi: 10.1039/C1SC00666E
45. [45]
  J. Qi, X. Xie, J. He, et al., Org. Biomol. Chem. 9(2011) 5948-5950. doi: 10.1039/c1ob05854a
46. [46]
  Z.Q. Liang, Z.H. Gao, W.Q. Jia, S. Ye, J. Chem Eur 21(2015) 1868-1872. doi: 10.1002/chem.v21.5
47. [47]
  K. Chand, A. Rajeshwari, M. Hiremathad, M.A. Singh, R.S. Keri Santos, Pharmacol. Rep. 69(2017) 281-295. doi: 10.1016/j.pharep.2016.11.007
48. [48]
  H. Khanam, Shamsuzzaman, Eur. J. Med. Chem. 97(2015) 483-504. doi: 10.1016/j.ejmech.2014.11.039
49. [49]
  A. Radadiya, A. Shah, Eur. J. Med. Chem. 97(2015) 356-376. doi: 10.1016/j.ejmech.2015.01.021
50. [50]
  V.N. Badavath, C. Nath, N.M. Ganta, Chin. Chem. Lett. 28(2017) 1528-1532. doi: 10.1016/j.cclet.2017.02.009
1. [1]
  Yiming Yang , Lichao Sun , Qingfeng Zhang . Plasmonic nanocrystals with intrinsic chirality: Biomolecule-directed synthesis and applications. Chinese Journal of Structural Chemistry, 2025, 44(1): 100467-100467. doi: 10.1016/j.cjsc.2024.100467
2. [2]
  Cong Gao , Zijian Zhu , Siwei Li , Zheng Xi , Qingqing Sun , Jie Han , Rong Guo . Chiral supramolecular catalysts of helical nanoribbon: More twist, higher enantioselectivity. Chinese Chemical Letters, 2025, 36(3): 109968-. doi: 10.1016/j.cclet.2024.109968
3. [3]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
4. [4]
  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
5. [5]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
6. [6]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
7. [7]
  Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
8. [8]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
9. [9]
  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
10. [10]
  Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
11. [11]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
12. [12]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
13. [13]
  Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
14. [14]
  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
15. [15]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
16. [16]
  Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
17. [17]
  Le Zhang , Hui-Yu Xie , Xin Li , Li-Ying Sun , Ying-Feng Han . SOMO-HOMO level conversion in triarylmethyl-cored N-heterocyclic carbene-Au(I) complexes triggered by selecting coordination halogens. Chinese Chemical Letters, 2024, 35(11): 109465-. doi: 10.1016/j.cclet.2023.109465
18. [18]
  Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
19. [19]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
20. [20]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(734)
HTML views(5)

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