Citation: Zhang Yanxia, Wu Xin-Yan, Han Jianwei. Chiral iminophosphorane catalyzed asymmetric Henry reaction of α, β-alkynyl ketoesters[J]. Chinese Chemical Letters, ;2019, 30(8): 1519-1522. doi: 10.1016/j.cclet.2019.04.042 shu

Chiral iminophosphorane catalyzed asymmetric Henry reaction of α, β-alkynyl ketoesters

Zhang Yanxia ^a,b ,
Wu Xin-Yan ^a,*, ,
Han Jianwei ^a,b,*,

a.
Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
b.
Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032, China

xinyanwu@ecust.edu.cn

jianweihan@ecust.edu.cn

Received Date: 27 January 2019
Revised Date: 11 April 2019
Accepted Date: 12 April 2019
Available Online: 22 August 2019

Figures(3)

α, β-Alkynyl ketoesters were introduced to the enantioselective Henry reaction (nitroaldol condensation) with nitromethane catalyzed by tartaric acid derived chiral iminophosphoranes. As such, a variety of optically active β-nitro-substituted tertiary alcohols bearing alkyne moieties were obtained in good to excellent yields (42%-99%) and moderate to good level of enantiomeric excess (up to 87% ee).
- Organocatalysis,
- Iminophosphorane,
- Nitroaldol,
- Henry reaction,
- Alkynyl ketoesters
1. [1]
  (a) L. Henry, Compt. Rend. Hebd. Seances Acad. Sci. 120 (1895) 1265-1267;
  (b) L. Henry, Bull. Soc. Chim. Fr. 13 (1895) 999-1003;
  (c) S. Zhang, Y. Li, Y. Xu, Z. Wang, Chin. Chem. Lett. 29 (2018) 873-883;
  (d) J. Boruwa, N. Gogoi, P.P. Saikia, N.C. Barua, Tetrahedron: Asymmetry 17 (2006) 3315-3326.
2. [2]
  (a) H. Sasai, T. Suzuki, S. Arai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 114 (1992) 4418-4420;
  (b) H. Sasai, T. Suzuki, N. Itoh, et al., J. Am. Chem. Soc. 115 (1993) 10372-10373.
3. [3]
  (a) F.A. Luzzio, Tetrahedron 57 (2001) 915-945;
  (b) C. Palomo, M. Oiarbide, A. Laso, Eur. J. Org. Chem. (2007) 2561-2564.
4. [4]
  R. Chinchilla, C. Nájera, P. Sánchez-Agulló, Tetrahedron:Asymmetry 5(1994) 1393-1402.
5. [5]
  (a) D. Ma, Q. Pan, F. Han, Tetrahedron Lett. 43 (2002) 9401-9403;
  (b) X.S. Li, Z.X. Shen, Y.W. Zhang, Chin. J. Org. Chem. 23 (2003) 566-569;
  (c) M.T. Allingham, A. Howard-Jones, P.J. Murphy, D.A. Thomas, P.W.R. Caulkett, Tetrahedron Lett. 44 (2003) 8677-8680;
  (d) Y. Sohtome, Y. Hashimoto, K. Nagasawa, Adv. Synth. Catal. 347 (2005) 1643-1648;
  (e) Y. Sohtome, N. Takemura, T. Iguchi, Y. Hashimoto, K. Nagasawa, Synlett (2006) 144-146;
  (f) Y. Sohtome, Y. Hashimoto, K. Nagasawa, Eur. J. Org. Chem. (2006) 2894-2897;
  (g) H. Ube, M. Terada, Bioorg. Med. Chem. Lett. 19 (2009) 3895-3898;
  (h) D. Leow, C.H. Tan, Chem. -Asian J. 4 (2009) 488-507.
6. [6]
  E.J. Corey, F.Y. Zhang, Angew. Chem. Int. Ed. 38(1999) 1931-1934. doi: 10.1002/(SICI)1521-3773(19990712)38:13/143.0.CO;2-4
7. [7]
  T. Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 125(2003) 2054-2055. doi: 10.1002/chin.200323032
8. [8]
  (a) T. Marcelli, R.N.S. van der Hass, J.H. van Maarseveen, H. Hiemstra, Synlett (2005) 2817-2819;
  (b) T. Marcelli, R.N.S. van der Hass, J.H. van Maarseveen, H. Hiemstra, Angew. Chem. Int. Ed. 45 (2006) 929-931;
  (c) P.K. Vijaya, S.M. Murugesan, A. Siva, Org. Biomol. Chem. 14 (2016) 10101-10109;
  (d) M. Liu, N. Ji, L. Wang, P. Liu, W. He, Tetrahedron Lett. 59 (2018) 999-1004;
  (e) J. Otevrel, P. Bobal, J. Org. Chem. 82 (2017) 8342-8358;
  (f) Y. Sohtome, N. Takemura, K. Takada, et al., Chem. -Asian J. 2 (2007) 1150-1160;
  (g) X. Liu, J. Jiang, M. Shi, Tetrahedron: Asymmetry 18 (2007) 2773-2781;
  (h) T. Okino, S. Nakamura, T. Furukawa, Y. Takemoto, Org. Lett. 6 (2004) 625-627;
  (i) T.P. Yoon, E.N. Jacobsen, Angew. Chem. Int. Ed. 44 (2005) 466-468.
9. [9]
  (a) S. Gao, G. Xi, N. Li, C. Wang, J. Ma, Chin. J. Org. Chem. 30 (2010) 1811-1819;
  (b) Y. Alvarez-Casao, E. Marques-Lopez, R.P. Herrera, Symmetry 3 (2011) 220-245.
10. [10]
  H. Li, B. Wang, L. Deng, J. Am. Chem. Soc. 128(2006) 732-733. doi: 10.1021/ja057237l
11. [11]
  (a) X. Chen, J. Wang, Y. Zhu, et al., Chem. -Eur. J. 14 (2008) 10896-10899;
  (b) T. Mandal, S. Samanta, C.G. Zhao, Org. Lett. 9 (2007) 943-945.
12. [12]
  (a) M. Vlatkovi c, L. Bernardi, E. Otten, B.L. Feringa, Chem. Commun. 50 (2014) 7773-7775;
  (b) M. Bandini, R. Sinisi, A. Umani-Ronchi, Chem. Commun. (2008) 4360-4362;
  (c) C. Palacio, S.J. Connon, Org. Lett. 13 (2011) 1298-1301.
13. [13]
  (a) M. Chennapuram, U.V.S. Reddy, C. Seki, et al., Eur. J. Org. Chem. (2017) 1638-1646;
  (b) M.Q. Li, J.X. Zhang, X.F. Huang, et al., Eur. J. Org. Chem. (2011) 5237-5241;
  (c) L. Liu, S. Zhang, F. Xue, et al., Chem. Eur. J. 17 (2011) 7791-7795;
  (d) P.S. Prathima, K. Srinivas, K. Balaswamy, et al., Tetrahedron: Asymmetry 22 (2011) 2099-2103.
14. [14]
  M.L. Zhang, D.F. Yue, Z.H. Wang, et al., Beilstein J. Org. Chem. 12(2016) 295-300. doi: 10.3762/bjoc.12.31
15. [15]
  (a) T. Shibata, N. Toshida, M. Yamasaki, S. Maekawa, K. Takagi, Tetrahedron 61 (2005) 9974-9979;
  (b) L.J. Deng, J. Liu, J.Q. Huang, et al., Synthesis (2007) 2565-2570;
  (c) K.H. Park, S.U. Song, Y.K. Chung, Tetrahedron Lett. 44 (2003) 2827-2830;
  (d) D.E. Kim, I.S. Kim, V. Ratovelomanana-Vidal, J.P. Genêt, N. Jeong, J. Org. Chem. 73 (2008) 7985-7989.
16. [16]
  (a) K. Yuan, S. Wang, Org. Lett. 19 (2017) 1462-1465;
  (b) M. Ueda, S. Sugita, A. Sato, T. Miyoshi, O. Miyata, J. Org. Chem. 77 (2012) 9344-9351.
17. [17]
  (a) M. Ueda, Y. Ikeda, A. Sato, et al., Tetrahedron 67 (2011) 4612-4615;
  (b) D. Sinha, A. Biswas, V.K. Singh, Org. Lett. 17 (2015) 3302-3305;
  (c) X. Wu, B. Wang, Y. Zhou, H. Liu, Org. Lett. 19 (2017) 1294-1297.
18. [18]
  S.A. Moteki, J. Han, S. Arimitsu, et al., Angew. Chem. Int. Ed. 51(2012) 1187-1190. doi: 10.1002/anie.201107239
19. [19]
  (a) J. Han, Y. Zhang, X.Y. Wu, H.N.C. Wong, Chem. Commun. 55 (2019) 397-400;
  (b) D. Uraguchi, K. Yamada, T. Ooi, Angew. Chem. Int. Ed. 54 (2015) 9954-9957;
  (c) D. Uraguchi, K. Koshimoto, T. Ooi, J. Am. Chem. Soc. 130 (2008) 10878-10879;
  (d) D. Uraguchi, T. Ito, S. Nakamura, T. Ooi, Chem. Sci. 1 (2010) 488-490;
  (e) L. Simon', R.S. Paton, J. Org. Chem. 82 (2017) 3855-3863;
  (f) M.A. Horwitz, B.P. Zavesky, J.I. Martinez-Alvarado, J.S. Johnson, Org. Lett. 18 (2016) 36-39;
  (g) T. Takeda, A. Kondoh, M. Terada, Angew. Chem. Int. Ed. 55 (2016) 4734-4737;
  (h) J. Yang, A.J.M. Farley, D.J. Dixon, Chem. Sci. 8 (2017) 606-610;
  (i) D. Uraguchi, R. Shibazaki, N. Tanaka, et al., Angew. Chem. Int. Ed. 57 (2018) 4732-4736.
20. [20]
  S. Wu, J. Tang, J. Han, D. Mao, X. Liu, X. Gao, J. Yu, L. Wang, Tetrahedron 70(2014) 5986-5992. doi: 10.1016/j.tet.2014.05.085
21. [21]
  (a) X. Gao, J. Han, L. Wang, Org. Lett. 17 (2015) 4596-4599;
  (b) X. Gao, J. Han, L. Wang, Org. Chem. Front. 3 (2016) 656-660;
  (c) X. Gao, J. Han, L. Wang, Synthesis 48 (2016) 2603-2611;
  (d) B. Li, Z.J. Xu, J. Han, Tetrahedron Lett. 59 (2018) 2412-2417.
1. [1]
  Zhenzhong MEI , Hongyu WANG , Xiuqi KANG , Yongliang SHAO , Jinzhong GU . Syntheses and catalytic performances of three coordination polymers with tetracarboxylate ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1795-1802. doi: 10.11862/CJIC.20240081
2. [2]
  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
3. [3]
  Ziyi Liu , Xunying Liu , Lubing Qin , Haozheng Chen , Ruikai Li , Zhenghua Tang . Alkynyl ligand for preparing atomically precise metal nanoclusters: Structure enrichment, property regulation, and functionality enhancement. Chinese Journal of Structural Chemistry, 2024, 43(11): 100405-100405. doi: 10.1016/j.cjsc.2024.100405
4. [4]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
5. [5]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
6. [6]
  Tiantian Long , Hongmei Luo , Jingbo Sun , Fengniu Lu , Yi Chen , Dong Xu , Zhiqin Yuan . Carbonization-engineered ultrafast chemical reaction on nanointerface. Chinese Chemical Letters, 2025, 36(3): 109728-. doi: 10.1016/j.cclet.2024.109728
7. [7]
  Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
8. [8]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
9. [9]
  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
10. [10]
  Zhao Li , Huimin Yang , Wenjing Cheng , Lin Tian . Recent progress of in situ/operando characterization techniques for electrocatalytic energy conversion reaction. Chinese Chemical Letters, 2024, 35(9): 109237-. doi: 10.1016/j.cclet.2023.109237
11. [11]
  Kunsong Hu , Yulong Zhang , Jiayi Zhu , Jinhua Mai , Gang Liu , Manoj Krishna Sugumar , Xinhua Liu , Feng Zhan , Rui Tan . Nano-engineered catalysts for high-performance oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(10): 109423-. doi: 10.1016/j.cclet.2023.109423
12. [12]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
13. [13]
  Guoliang Gao , Guangzhen Zhao , Guang Zhu , Bowen Sun , Zixu Sun , Shunli Li , Ya-Qian Lan . Recent advancements in noble-metal electrocatalysts for alkaline hydrogen evolution reaction. Chinese Chemical Letters, 2025, 36(1): 109557-. doi: 10.1016/j.cclet.2024.109557
14. [14]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
15. [15]
  Jialin Cai , Yizhe Chen , Ruiwen Zhang , Cheng Yuan , Zeyu Jin , Yongting Chen , Shiming Zhang , Jiujun Zhang . Interfacial Pt-N coordination for promoting oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(2): 110255-. doi: 10.1016/j.cclet.2024.110255
16. [16]
  Yan Guo , Hongtao Bian , Le Yu , Jiani Ma , Yu Fang . Photochemical reaction mechanism of benzophenone protected guanosine at N7 position. Chinese Chemical Letters, 2025, 36(3): 109971-. doi: 10.1016/j.cclet.2024.109971
17. [17]
  Xuan Liu , Qing Li . Tailoring interatomic active sites for highly selective electrocatalytic biomass conversion reaction. Chinese Chemical Letters, 2025, 36(4): 110670-. doi: 10.1016/j.cclet.2024.110670
18. [18]
  Xiao Li , Wanqiang Yu , Yujie Wang , Ruiying Liu , Qingquan Yu , Riming Hu , Xuchuan Jiang , Qingsheng Gao , Hong Liu , Jiayuan Yu , Weijia Zhou . Metal-encapsulated nitrogen-doped carbon nanotube arrays electrode for enhancing sulfion oxidation reaction and hydrogen evolution reaction by regulating of intermediate adsorption. Chinese Chemical Letters, 2024, 35(8): 109166-. doi: 10.1016/j.cclet.2023.109166
19. [19]
  Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO₂ nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
20. [20]
  Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(643)
HTML views(22)

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