Citation: Kui Tian, Gongyi Liu, Xiu-Qin Dong. Facile access to chiral 1-pyrrolines through Rh-catalyzed enantioselective partial hydrogenation of unprotected simple pyrroles[J]. Chinese Chemical Letters, ;2022, 33(12): 5092-5095. doi: 10.1016/j.cclet.2022.04.027 shu

Facile access to chiral 1-pyrrolines through Rh-catalyzed enantioselective partial hydrogenation of unprotected simple pyrroles

Kui Tian ^{a, 1} ,
Gongyi Liu ^{a, 1} ,
Xiu-Qin Dong ^{a, b, *,}

a.
Engineering Research Centre of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China
b.
Suzhou Institute of Wuhan University, Suzhou 215123, China

xiuqindong@whu.edu.cn

Received Date: 29 December 2021
Revised Date: 9 April 2022
Accepted Date: 12 April 2022
Available Online: 15 April 2022

Figures(6)

Highly enantioselective Rh-catalyzed partial hydrogenation of unprotected simple 2-alkyl-5-aryl-disubstituted pyrroles has been successfully developed, generating a series of chiral 1-pyrroline derivatives generally with excellent results (95%–99% yields, 91%–96% ee). Moreover, 2,5-aryl-1H-pyrroles were hydrogenated well in high yields and good enantioselectivities. This efficient protocol features easily accessible substrates, wide substrate scope, well functional group compatibility, commercially available rhodium precursor and chiral ligand. It provides a versatile route to access chiral 1-pyrroline derivatives that are of great importance in organic synthesis and pharmaceutical chemistry.
- Chiral 1-pyrrolines,
- Partial hydrogenation,
- Unprotected simple pyrroles,
- Regioselectivity,
- Enantioselectivity
1. [1]
  X.C. Cai, B.B. Snider, J. Org. Chem. 78 (2013) 12161–12175. doi: 10.1021/jo402178r
2. [2]
  L. Chevolot, A.M. Chevolot, M. Gajhede, et al., J. Am. Chem. Soc. 107 (1985) 4542–4543. doi: 10.1021/ja00301a027
3. [3]
  H. Abe, S. Aoyagi, C. Kibayashi, J. Am. Chem. Soc. 127 (2005) 1473–1480. doi: 10.1021/ja040213e
4. [4]
  N. Toda, M. Ori, K. Takami, K. Tago, H. Kogen, Org. Lett. 5 (2003) 269–271. doi: 10.1021/ol027215t
5. [5]
  E. O'Reilly, C. Iglesias, D. Ghislieri, et al., Angew. Chem. Int. Ed. 53 (2014) 2447–2450. doi: 10.1002/anie.201309208
6. [6]
  X. Bai, L. Li, Z. Xu, et al., Chem. Eur. J. 22 (2016) 10399–10404. doi: 10.1002/chem.201601945
7. [7]
  A. Viso, N.E. Lee, S.L. Buchwald, J. Am. Chem. Soc. 116 (1994) 9373–9374. doi: 10.1021/ja00099a082
8. [8]
  J. Yun, S.L. Buchwald, Chirality 12 (2000) 476–478. doi: 10.1002/(SICI)1520-636X(2000)12:5/6<476::AID-CHIR31>3.0.CO;2-B
9. [9]
  C.X. Zhuo, Y. Zhou, S.L. You, J. Am. Chem. Soc. 136 (2014) 6590–6593. doi: 10.1021/ja5028138
10. [10]
  C. Zheng, C.X. Zhuo, S.L. You, J. Am. Chem. Soc. 136 (2014) 16251–16259. doi: 10.1021/ja5080135
11. [11]
  V. Háda, A. Tungler, L. Szepesy, Appl. Catal. A: Gen. 210 (2001) 165–171. doi: 10.1016/S0926-860X(00)00795-X
12. [12]
  R. Kuwano, M. Kashiwabara, M. Ohsumi, H. Kusano, J. Am. Chem. Soc. 130 (2008) 808–809. doi: 10.1021/ja7102422
13. [13]
  D.S. Wang, Z.S. Ye, Q.A. Chen, et al., J. Am. Chem. Soc. 133 (2011) 8866–8869. doi: 10.1021/ja203190t
14. [14]
  P. Tang, H. Wang, W. Zhang, F.E. Chen, Green Synth. Catal. 1 (2020) 26–41. doi: 10.1016/j.gresc.2020.05.006
15. [15]
  Y.M. He, F.T. Song, Q.H. Fan, Top. Curr. Chem. 343 (2014) 145–190. doi: 10.1007/128_2013_480
16. [16]
  Q.A. Chen, Z.S. Ye, Y. Duan, Y.G. Zhou, Chem. Soc. Rev. 42 (2013) 497–511. doi: 10.1039/C2CS35333D
17. [17]
  M.P. Wiesenfeldt, Z. Nairoukh, T. Dalton, F. Glorius, Angew. Chem. 131 (2019) 10460–10476. doi: 10.1002/anie.201814471
18. [18]
  D.S. Wang, Q.A. Chen, S.M. Lu, Y.G. Zhou, Chem. Rev. 112 (2012) 2557–2590. doi: 10.1021/cr200328h
19. [19]
  R. Kuwano, K. Sato, T. Kurokawa, D. Karube, Y. Ito, J. Am. Chem. Soc. 122 (2000) 7614–7615. doi: 10.1021/ja001271c
20. [20]
  Z.S. Yang, F. Chen, Y.M. He, N.F. Yang, Q.H. Fan, Angew. Chem. Int. Ed. 55 (2016) 13863–13866. doi: 10.1002/anie.201607890
21. [21]
  N. Ortega, S. Urban, B. Beiring, F. Glorius, Angew. Chem. Int. Ed. 51 (2012) 1710–1713. doi: 10.1002/anie.201107811
22. [22]
  D. Moock, T. Moock, T.J. Hu, T. Gallagher, F. Glorius, Angew. Chem. Int. Ed. 60 (2021) 13677–13681. doi: 10.1002/anie.202103910
23. [23]
  N. Ortega, D.D. Tang, S. Urban, D.B. Zhao, F. Glorius, Angew. Chem. Int. Ed. 52 (2013) 9500–9503. doi: 10.1002/anie.201302218
24. [24]
  B.V.M. Teodoro, J.T.M. Correia, F. Coelho, J. Org. Chem. 80 (2015) 2529–2538. doi: 10.1021/jo502471q
25. [25]
  W.B. Wang, S.M. Lu, P.Y. Yang, X.W. Han, Y.G. Zhou, J. Am. Chem. Soc. 125 (2003) 10536–10537. doi: 10.1021/ja0353762
26. [26]
  Z. Han, G. Liu, X. Yang, X.Q. Dong, X. Zhang, ACS Catal. 11 (2021) 7281–7291. doi: 10.1021/acscatal.1c01353
27. [27]
  J. Wen, R. Tan, S. Liu, Q. Zhao, X. Zhang, Chem. Sci. 7 (2016) 3047–3051. doi: 10.1039/C5SC04712A
28. [28]
  M. Rueping, A.P. Antonchick, T. Theissmann, Angew. Chem. Int. Ed. 45 (2006) 3683–3686. doi: 10.1002/anie.200600191
29. [29]
  S.M. Lu, Y.Q. Wang, X.W. Han, Y.G. Zhou, Angew. Chem. Int. Ed. 45 (2006) 2260–2263. doi: 10.1002/anie.200503073
30. [30]
  D.B. Zhao, F. Glorius, Angew. Chem. Int. Ed. 52 (2013) 9616–9618. doi: 10.1002/anie.201304756
31. [31]
  W.J. Tang, L.J. Xu, Q.H. Fan, et al., Angew. Chem. Int. Ed. 48 (2009) 9135–9138. doi: 10.1002/anie.200904518
32. [32]
  Q.A. Chen, D.S. Wang, Y.G. Zhou, et al., J. Am. Chem. Soc. 133 (2011) 6126–6129. doi: 10.1021/ja200723n
33. [33]
  S.A. Raynor, J.M. Thomas, R. Raja, et al., Chem. Commun. (2000) 1925–1926. doi: 10.1039/B005689H
34. [34]
  Z.S. Ye, M.W. Chen, Q.A. Chen, et al., Angew. Chem. Int. Ed. 51 (2012) 10181–10184. doi: 10.1002/anie.201205187
35. [35]
  W.X. Huang, C.B. Yu, Y. Ji, L.J. Liu, Y.G. Zhou, ACS Catal. 6 (2016) 2368–2371. doi: 10.1021/acscatal.5b02625
36. [36]
  Z. Nairoukh, M. Wollenburg, C. Schlepphorst, K. Bergander, F. Glorius, Nat. Chem. 11 (2019) 264–270. doi: 10.1038/s41557-018-0197-2
37. [37]
  S. Kaiser, S.P. Smidt, A. Pfaltz, Angew. Chem. Int. Ed. 45 (2006) 5194–5197. doi: 10.1002/anie.200601529
38. [38]
  P. Feiertag, M. Albert, U. Nettekoven, F. Spindler, Org. Lett. 8 (2006) 4133–4135. doi: 10.1021/ol061681r
39. [39]
  Q. Zhao, S. Li, K. Huang, R. Wang, X. Zhang, Org. Lett. 15 (2013) 4014–4017. doi: 10.1021/ol401816y
1. [1]
  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
2. [2]
  Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
3. [3]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
4. [4]
  Zhiwei Zhong , Yanbin Huang , Wantai Yang . A simple photochemical method for surface fluorination using perfluoroketones. Chinese Chemical Letters, 2024, 35(5): 109339-. doi: 10.1016/j.cclet.2023.109339
5. [5]
  Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
6. [6]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
7. [7]
  Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
8. [8]
  Yu Yan , Jiawei Song , Dongdong Liu , Zihan Liu , Jialing Cheng , Zhiyang Chen , Yanfang Yang , Weizhe Jiang , Hongliang Wang , Jun Ye , Yuling Liu . Simple and versatile in situ thermo-sensitive hydrogel for rectal administration of SZ-A to alleviate inflammation and repair mucosal barrier in ulcerative colitis. Chinese Chemical Letters, 2024, 35(6): 109736-. doi: 10.1016/j.cclet.2024.109736
9. [9]
  Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
10. [10]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
11. [11]
  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
12. [12]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
13. [13]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
14. [14]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
15. [15]
  Zhao-Xia Lian , Xue-Zhi Wang , Chuang-Wei Zhou , Jiayu Li , Ming-De Li , Xiao-Ping Zhou , Dan Li . Producing circularly polarized luminescence by radiative energy transfer from achiral metal-organic cage to chiral organic molecules. Chinese Chemical Letters, 2024, 35(8): 109063-. doi: 10.1016/j.cclet.2023.109063
16. [16]
  Yongjing Deng , Feiyang Li , Zijian Zhou , Mengzhu Wang , Yongkang Zhu , Jianwei Zhao , Shujuan Liu , Qiang Zhao . Chiral induction and Sb³⁺ doping in indium halides to trigger second harmonic generation and circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(8): 109085-. doi: 10.1016/j.cclet.2023.109085
17. [17]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
18. [18]
  Xue-Zhi Wang , Yi-Tong Liu , Chuang-Wei Zhou , Bei Wang , Dong Luo , Mo Xie , Meng-Ying Sun , Yong-Liang Huang , Jie Luo , Yan Wu , Shuixing Zhang , Xiao-Ping Zhou , Dan Li . Amplified circularly polarized luminescence of chiral metal-organic frameworks via post-synthetic installing pillars. Chinese Chemical Letters, 2024, 35(10): 109380-. doi: 10.1016/j.cclet.2023.109380
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(533)
HTML views(12)

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