Construction of chiral 3-alkenyl-3-substituted oxindoles by stereoselective direct alkenylation of isatin derivatives and 3-vinylindoles
-
* Corresponding author.
E-mail address: zwang3@ustc.edu.cn (Z. Wang)
Citation: Xiang Sun, Kuiliang Li, Shuangshuang Zhao, Zhenggen Zha, Zhiyong Wang. Construction of chiral 3-alkenyl-3-substituted oxindoles by stereoselective direct alkenylation of isatin derivatives and 3-vinylindoles[J]. Chinese Chemical Letters, ;2022, 33(12): 5106-5110. doi: 10.1016/j.cclet.2022.04.032
S. Mohammadi, R. Heiran, R.P. Herrera, et al., ChemCatChem 5 (2013) 2131–2148.
doi: 10.1002/cctc.201300050
G.S. Singh, Z.Y. Desta, Chem. Rev. 112 (2012) 6104–6155.
doi: 10.1021/cr300135y
F. Zhou, Y. Liu, J. Zhou, Adv. Synth. Catal. 352 (2010) 1381–1407.
doi: 10.1002/adsc.201000161
F.V. Nussbaum, S.J. Danishefsky, Angew. Chem. Int. Ed. 39 (2000) 2175–2178.
doi: 10.1002/1521-3773(20000616)39:12<2175::AID-ANIE2175>3.0.CO;2-J
X. Jiang, Y. Sun, J. Yao, et al., Adv. Synth. Catal. 354 (2012) 917–925.
doi: 10.1002/adsc.201100792
Y. Sun, J. Liu, T. Sun, et al., Sci. Rep. 4 (2014) 4372.
M. Ochi, K. Kawasaki, H. Kataoka, et al., Biochem. Biophys. Res. Commun. 283 (2001) 1118–1123.
doi: 10.1006/bbrc.2001.4911
J.C. Pelt-Koops, H.E. Pett, W. Graumans, et al., Antimicrob. Agents Chemother. 56 (2012) 3544–3548.
doi: 10.1128/AAC.06377-11
X. Liu, H. Zheng, C. Xu, et al., Angew. Chem. Int. Ed. 54 (2015) 10958–10962.
doi: 10.1002/anie.201505717
H. Turner, Futur. Med. Chem. 8 (2016) 227–238.
doi: 10.4155/fmc.15.177
J.F.M. da Silva, S. J Garden, A. C Pinto, J. Braz. Chem. Soc. 12 (2001) 273.
doi: 10.1590/S0103-50532001000300002
J. Bergman, J.O. Lindstrom, U. Tilstam, Tetrahedron 41 (1988) 2879–2881.
doi: 10.1016/s0040-4020(01)96609-8
Q. Chen, Y. Tang, T. Huang, et al., Angew. Chem. Int. Ed. 55 (2016) 5286–5289.
doi: 10.1002/anie.201600711
G. Wang, X. Liu, Y. Chen, et al., ACS Catal. 6 (2016) 2482–2486.
doi: 10.1021/acscatal.6b00294
J. Xu, J. Peng, C He, H. Ren, Org. Chem. Front. 6 (2019) 172–176.
doi: 10.1039/C8QO01085D
J. Wang, Q Zhang, Y Li, et al., Chem. Commun. 56 (2020) 261–264.
doi: 10.1039/C9CC07944K
J. Duan, Y. Mao, A. Xian, et al., Chem. Commun. 57 (2021) 3379–3382.
doi: 10.1039/D0CC07995B
J. Li, Y. Li, J. Sun, et al., Chem. Commun. 55 (2019) 6309–6312.
doi: 10.1039/C9CC02159K
Y. Liu, B. Wang, J. Cao, et al., J. Am. Chem. Soc. 132 (2010) 15176–15178.
doi: 10.1021/ja107858z
Y. Huang, R. Huang, Y. Zhao, J. Am. Chem. Soc. 138 (2016) 6571–6576.
doi: 10.1021/jacs.6b02372
B. Xiang, T.F. Xu, L. Wu, et al., J. Org. Chem. 81 (2016) 3929–3935.
doi: 10.1021/acs.joc.6b00358
R.R. Liu, D.J. Wang, L. Wu, et al., ACS Catal. 5 (2015) 6524–6528.
doi: 10.1021/acscatal.5b01793
K. Li, X. Sun, L. Li, et al., Chem. Eur. J. 27 (2021) 581–584.
doi: 10.1002/chem.202003510
F. Guo, G. Lai, S. Xiong, et al., Chem. Eur. J. 16 (2010) 6438–6441.
doi: 10.1002/chem.201000540
C. Li, F. Guo, K. Xu, et al., Org. Lett. 16 (2014) 3192–3195.
doi: 10.1021/ol501086q
J. Sun, Y. Hu, Y. Li, et al., J. Org. Chem. 82 (2017) 5102–5110.
doi: 10.1021/acs.joc.7b00159
Y. Gui, Y. Li, J. Sun, et al., J. Org. Chem. 83 (2018) 7491–7499.
doi: 10.1021/acs.joc.8b01141
J. Sun, Y. Gui, Y. Huang, et al., ACS Omega 5 (2020) 11962–11970.
doi: 10.1021/acsomega.9b04115
X. Liang, Y. Gui, K. Li, et al., Chem. Commun. 56 (2020) 11118–11121.
doi: 10.1039/D0CC04410E
X. Li, W. Yuan, S. Tang, et al., Org. Lett. 19 (2017) 1120–1123.
doi: 10.1021/acs.orglett.7b00143
X. Li, W. Hu, Q. Xiong, et al., Adv. Synth. Catal. 361 (2019) 1803–1807.
doi: 10.1002/adsc.201801705
Y. Huang, X. Li, L. Fu, Q. Guo, Org. Lett. 18 (2016) 6200–6203.
doi: 10.1021/acs.orglett.6b03257
W. Hu, X. Li, W. Gui, et al., Org. Lett. 21 (2019) 10090–10093.
doi: 10.1021/acs.orglett.9b04063
X. Guan, H. Zhang, J. Gao, et al., J. Org. Chem. 84 (2019) 12562–12572.
doi: 10.1021/acs.joc.9b02024
J.H. Xue, M. Shi, F. Yu, et al., Org. Lett. 18 (2016) 3874–3877.
doi: 10.1021/acs.orglett.6b01880
Y.W. Sun, Z.S. Wang, S.F. Wu, Y.C. Zhang, F. Shi, Green Synth. Catal. 3 (2022) 84–88.
doi: 10.1016/j.gresc.2021.11.003
G.Y. Lai, S.J. Wang, Z.Y. Wang, Tetrahedron: Asymmetry 19 (2008) 1813–1819.
doi: 10.1016/j.tetasy.2008.06.036
F. Guo, D. Chang, G. Lai, et al., Chem. Eur. J. 17 (2011) 11127–11130.
doi: 10.1002/chem.201102206
C. Y. Legault, C.Y. Lview, 1.0b, Universit de Sherbrooke, 2009, http://www.cylview.org.
Z. Guan, H. Wang, Y. Huang, et al., Org. Lett. 21 (2019) 4619–4622.
doi: 10.1021/acs.orglett.9b01518
Z. Chen, W. Bai, S. Wang, et al., Angew. Chem. Int. Ed. 52 (2013) 9781–9785.
doi: 10.1002/anie.201304557
Z. Zeng, X Xun, L Huang, et al., Green. Chem. 20 (2018) 2477–2480.
doi: 10.1039/C8GC00478A
G. Guo, Y. Yuan, S. Wan, et al., Org. Chem. Front. 8 (2021) 2990–2996.
doi: 10.1039/D1QO00148E
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
Yifan LIU , Zhan ZHANG , Rongmei ZHU , Ziming QIU , Huan PANG . A three-dimensional flower-like Cu-based composite and its low-temperature calcination derivatives for efficient oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 979-990. doi: 10.11862/CJIC.20240008
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
Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
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
Xiaoming Fu , Haibo Huang , Guogang Tang , Jingmin Zhang , Junyue Sheng , Hua Tang . Recent advances in g-C3N4-based direct Z-scheme photocatalysts for environmental and energy applications. Chinese Journal of Structural Chemistry, 2024, 43(2): 100214-100214. doi: 10.1016/j.cjsc.2024.100214
Wenjuan Jin , Zelong Chen , Yi Wang , Jiaxuan Li , Jiahui Li , Yuxin Pei , Zhichao Pei . Nano metal-photosensitizer based on Aza-BODIPY-Cu complex for CDT-enhanced dual phototherapy. Chinese Chemical Letters, 2024, 35(7): 109328-. doi: 10.1016/j.cclet.2023.109328
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
Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
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
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
Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe2O3 and NO2 with 2D-COS: The role of SDS, UV and SO2. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
Fangwen Peng , Zhen Luo , Yingjin Ma , Haibo Ma . Theoretical study of aromaticity reversal in dimethyldihydropyrene derivatives. Chinese Journal of Structural Chemistry, 2024, 43(5): 100273-100273. doi: 10.1016/j.cjsc.2024.100273
Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
Xinqiong Li , Guocheng Rao , Xi Peng , Chan Yang , Yanjing Zhang , Yan Tian , Xianghui Fu , Jia Geng . Direct detection of C9orf72 hexanucleotide repeat expansions by nanopore biosensor. Chinese Chemical Letters, 2024, 35(5): 109419-. doi: 10.1016/j.cclet.2023.109419
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
Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825