Citation: Sun Haiyun, Li Yuan, Liu Wei, Zheng Yang, He Zhengjie. Organocatalytic asymmetric cascade cyclization reaction of o-hydroxy cinnamaldehydes with diphenylphosphine oxide[J]. Chinese Chemical Letters, ;2018, 29(11): 1625-1628. doi: 10.1016/j.cclet.2018.01.026 shu

Organocatalytic asymmetric cascade cyclization reaction of o-hydroxy cinnamaldehydes with diphenylphosphine oxide

Sun Haiyun ^a ,
Li Yuan ^a ,
Liu Wei ^a ,
Zheng Yang ^a ,
He Zhengjie ^a,b,,

a.
The State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
b.
Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300071, China

Corresponding author: He Zhengjie, zhengjiehe@nankai.edu.cn
Received Date: 6 December 2017
Revised Date: 4 January 2018
Accepted Date: 15 January 2018
Available Online: 1 December 2018

Figures(4)

A highly stereoselective asymmetric cascade cyclization reaction between o-hydroxycinnamaldehydes and diphenylphosphine oxide has been achieved with 84%-99% ee and 7:1-20:1 dr under the catalysis of L-diarylprolinol silyl ether. This reaction provides a facile access to highly enantioenriched 4-diphenylphosphinyl chroman-2-ols. It also represents a novel organocatalytic asymmetric phosphaMichael addition of α, β-unsaturated aldehydes with pentavalent P-nucleophiles.
- Organocatalysis,
- Asymmetric catalysis,
- Cyclization reaction,
- Phospha-Michael addition,
- Cascade reaction
1. [1]
  B. List, Asymmetric Organocatalysis, Springer, Berlin, 2010.
2. [2]
  W.J. Liu, N. Li, L.Z. Gong, Top. Organomet. Chem. 36(2011) 153-206. doi: 10.1007/978-3-642-19472-6
3. [3]
  J.F. Briere, S. Oudeyer, V. Dalla, V. Levacher, Chem. Soc. Rev. 41(2012) 1696-1707. doi: 10.1039/C1CS15200A
4. [4]
  J.D. Duan, P.F. Li, Sci. Catal. Technol. 4(2014) 311-320. doi: 10.1039/C3CY00739A
5. [5]
  X. Fang, C.J. Wang, Chem. Commun. 51(2015) 1185-1197. doi: 10.1039/C4CC07909D
6. [6]
  J. Franzen, M. Marigo, D. Fielenbach, et al., J. Am. Chem. Soc.127(2005) 18296-18304. doi: 10.1021/ja056120u
7. [7]
  K.L. Jensen, G. Dickmeiss, H. Jiang, L. Albrecht, K.A. Jørgensen, Acc. Chem. Res. 45(2012) 248-264. doi: 10.1021/ar200149w
8. [8]
  B.S. Donslund, T.K. Johansen, P.H. Poulsen, K.S. Halskov, K.A. Jørgensen, Angew. Chem. Int. Ed. 54(2015) 13860-13874. doi: 10.1002/anie.201503920
9. [9]
  R.L. Hildebrand, The Role of Phosphonates in Living System, CRC, Boca Raton, 1983.
10. [10]
  S.C. Fields, Tetrahedron 55(1999) 12237-12273. doi: 10.1016/S0040-4020(99)00701-2
11. [11]
  J.I.G. Cadogan, Organophosphorus Reagents in Organic Synthesis, Academic Press London, 1979.
12. [12]
  P.J. Murphy, Organophosphorus Reagents, Oxford University Press, Oxford, 2004.
13. [13]
  M. Mikołajczyk, P. Bałczewski, Top. Curr. Chem. 223(2003) 161-214. doi: 10.1007/3-540-46100-0
14. [14]
  A. Borner, Phosphorus Ligands in Asymmetric Catalysis:Synthesis and Applications, Wiley-VCH Weinheim, 2008.
15. [15]
  D. Enders, A. Saint-Dizier, M.I. Lannou, A. Lenzen, Eur. J. Org. Chem (2005) 29-49.
16. [16]
  L. Albrecht, A. Albrecht, H. Krawczyk, K.A. Jørgensen, Chem. Eur. J. 16(2010) 28-48. doi: 10.1002/chem.v16:1
17. [17]
  M.M. Heravi, P. Hajiabbasi, Mol. Divers 18(2014) 411-439. doi: 10.1007/s11030-013-9494-2
18. [18]
  D. Zhao, L. Mao, D. Yang, R. Wang, J. Org. Chem. 75(2010) 6756-6763. doi: 10.1021/jo1014917
19. [19]
  D. Zhao, Y. Wang, L. Mao, R. Wang, Chem. Eur. J. 15(2009) 10983-10987. doi: 10.1002/chem.200901901
20. [20]
  G. Bartoli, M. Bosco, A. Carlone, et al., Chem. Commun (2007) 722-724.
21. [21]
  A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. Int. Ed. 46(2007) 4504-4506. doi: 10.1002/(ISSN)1521-3773
22. [22]
  I. Ibrahem, R. Rios, J. Vesely, et al., Angew. Chem. Int. Ed. 46(2007) 4507-4510. doi: 10.1002/(ISSN)1521-3773
23. [23]
  E. Maerten, S. Cabrera, A. Kjærsgaard, K.A. Jørgensen, J. Org. Chem. 72(2007) 8893-8903. doi: 10.1021/jo7018587
24. [24]
  I. Ibrahem, P. Hammar, J. Vesely, et al., Adv. Synth. Catal. 350(2008) 1875-1884. doi: 10.1002/adsc.v350:11/12
25. [25]
  X. Fu, Z. Jiang, C.H. Tan, Chem. Commun. (2007) 5058-5060.
26. [26]
  M. Terada, T. Ikehara, H. Ube, J. Am. Chem. Soc. 129(2007) 14112-14113. doi: 10.1021/ja0746619
27. [27]
  J. Wang, L.D. Heikkinen, H. Li, et al., Adv. Synth. Catal. 349(2007) 1052-1056. doi: 10.1002/(ISSN)1615-4169
28. [28]
  Y. Zhu, J.P. Malerich, V.H. Rawal, Angew. Chem. Int. Ed. 49(2010) 153-156. doi: 10.1002/anie.200904779
29. [29]
  Y. Lee, S.W. Seo, S.G. Kim, Adv. Synth. Catal. 353(2011) 2671-2675. doi: 10.1002/adsc.v353.14/15
30. [30]
  K.S. Choi, S.G. Kim, Eur. J. Org. Chem. (2012) 1119-1122.
31. [31]
  B. Zhang, L. Cai, H. Song, Z. Wang, Z. He, Adv. Synth. Catal. 352(2010) 97-102. doi: 10.1002/adsc.v352:1
32. [32]
  H. Sun, B. Zhang, X. Chen, Z. He, Synthesis 49(2017) 2205-2214. doi: 10.1055/s-0036-1588716
33. [33]
  V. Sharma, P. Kumar, D. Pathak, J. Heterocyclic Chem. 47(2010) 491-502.
34. [34]
  J. Pan, Y. Wang, S. Chen, et al., Tetrahedron 72(2016) 240-246. doi: 10.1016/j.tet.2015.11.042
1. [1]
  Qian Liu , Yi Shi , Kaiya Wang , Xiao-Yu Hu . Tailoring cascade hydrolysis and cyclization efficiency in confined spaces via spatial and electrostatic regulation. Chinese Chemical Letters, 2025, 36(12): 111462-. doi: 10.1016/j.cclet.2025.111462
2. [2]
  Ji-Jia Zhou , Li-Gao Liu , Zhen-Tao Zhang , Hao-Xuan Dong , Xin Lu , Zhou Xu , Xin-Qi Zhu , Bo Zhou , Long-Wu Ye . Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement. Chinese Chemical Letters, 2025, 36(9): 110870-. doi: 10.1016/j.cclet.2025.110870
3. [3]
  Tengfei Xuan , Yuan Pan , Zhenyu Shi , Yang Wang . Organocatalytic asymmetric synthesis of oxazolines from N-acylimines. Chinese Chemical Letters, 2025, 36(6): 110352-. doi: 10.1016/j.cclet.2024.110352
4. [4]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
5. [5]
  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
6. [6]
  Yanxin Jiang , Kwai Wun Cheng , Zhiping Yang , Jun (Joelle) Wang . Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes. Chinese Chemical Letters, 2025, 36(5): 110231-. doi: 10.1016/j.cclet.2024.110231
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]
  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
9. [9]
  Yan-Bo Li , Yi Li , Liang Yin . Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction. Chinese Chemical Letters, 2024, 35(7): 109294-. doi: 10.1016/j.cclet.2023.109294
10. [10]
  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
11. [11]
  Chengyao Zhao , Jingyuan Liao , Yuxiang Zhu , Yiying Zhang , Lianjie Zhai , Junrong Huang , Hengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337
12. [12]
  Kai Zhu , Lei Yang , Yang Yang , Yanqi Wu , Fengzhi Zhang . Recent advances toward the catalytic enantioselective synthesis of planar chiral cyclophanes. Chinese Chemical Letters, 2025, 36(7): 110678-. doi: 10.1016/j.cclet.2024.110678
13. [13]
  Jun Liu , Zhaoyu Feng , Renming Pan , Xiaolong Yu , Meijuan Zhou , Gang Zhao , Hongyu Wang . Enantioselective regulation to coronal polyheterocyclic compounds via phosphonium salt-catalyzed cycloadditions of azomethine imines with γ-butenolides. Chinese Chemical Letters, 2025, 36(8): 110647-. doi: 10.1016/j.cclet.2024.110647
14. [14]
  Guodong Wang , Mengying Jia , Haitao Liu , Yong Liu , Zhiguo Zhang , Xianxiu Xu . Expeditious synthesis and applications of isoquinoline ring-modified Quinap derivatives. Chinese Chemical Letters, 2025, 36(8): 110705-. doi: 10.1016/j.cclet.2024.110705
15. [15]
  Bingbing Dong , Junmin Zhang , Xiang-Yu Ye , Xuan Huang , Yonggui Robin Chi . Catalytic construction of P-stereogenic center via phosphorus-centered nucleophilic substitution. Chinese Chemical Letters, 2025, 36(9): 111052-. doi: 10.1016/j.cclet.2025.111052
16. [16]
  Yi-Kao Xu , Guo-Ping Luo , Liang-Bin Hu , Wei-Min He . Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes. Chinese Chemical Letters, 2025, 36(8): 111226-. doi: 10.1016/j.cclet.2025.111226
17. [17]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
18. [18]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
19. [19]
  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
20. [20]
  Yue Sun , Yingnan Zhu , Jiahang Si , Ruikang Zhang , Yalan Ji , Jinjie Fan , Yuze Dong . Glucose-activated nanozyme hydrogels for microenvironment modulation via cascade reaction in diabetic wound. Chinese Chemical Letters, 2025, 36(4): 110012-. doi: 10.1016/j.cclet.2024.110012

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1380)
HTML views(56)

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