Absolute asymmetric synthesis driven by circularly polarized light
-
* Corresponding author.
E-mail address: liyann@sdfmu.edu.cn (Y. Li).
Citation:
Chenlu He, Yan Li. Absolute asymmetric synthesis driven by circularly polarized light[J]. Chinese Chemical Letters,
;2023, 34(8): 108077.
doi:
10.1016/j.cclet.2022.108077
A. Lazcano, S.L. Miller, Cell 85 (1996) 793–798.
doi: 10.1016/S0092-8674(00)81263-5
J.R. Cronin, S. Pizzarello, Science 275 (1997) 951–955.
doi: 10.1126/science.275.5302.951
G. Balavoine, A. Moradpour, H.B. Kagan, J. Am. Chem. Soc. 96 (1974) 5152–5158.
doi: 10.1021/ja00823a023
N.P.M. Huck, W.F. Jager, B. de Lange, B.L. Feringa, Science 273 (1996) 1686–1688.
doi: 10.1126/science.273.5282.1686
C. Wang, T. Jiang, X. Ma, Chin. Chem. Lett. 31 (2020) 2921–2924.
doi: 10.1016/j.cclet.2020.03.021
L. Liu, J. Chen, T. Yu, et al., Chin. Chem. Lett.34 (2023) 107649.
doi: 10.1016/j.cclet.2022.06.072
C. Tu, W. Wu, W. Liang, et al., Angew. Chem. Int. Ed. 61 (2022) e202203541.
doi: 10.1002/anie.202203541
H. Rau, Chem. Rev. 83 (1983) 535–547.
doi: 10.1021/cr00057a003
Y. Inoue, Chem. Rev. 92 (1992) 741–770.
doi: 10.1021/cr00013a001
S. Allenmark, J. Gawronski, Chirality 20 (2008) 606–608.
doi: 10.1002/chir.20524
A. Moradpour, J.F. Nicoud, G. Balavoine, H. Kagan, G. Tsoucaris, J. Am. Chem. Soc. 93 (1971) 2353–2354.
doi: 10.1021/ja00738a061
W.J. Bernstein, M. Calvin, O. Buchardt, J. Am. Chem. Soc. 94 (1972) 494–498.
doi: 10.1021/ja00757a029
H. Kagan, A. Moradpour, J.F. Nicoud, et al., Tetrahedron Lett. 27 (1971) 2479–2482.
R.D. Richardson, M.G.J. Baud, C.E. Weston, et al., Chem. Sci. 6 (2015) 3853–3862.
doi: 10.1039/C4SC03897E
Y. Zhang, G.B. Schuster, J. Org. Chem. 60 (1995) 7192–7197.
doi: 10.1021/jo00127a026
I. Sato, R. Sugie, Y. Matsueda, Y. Furumura, K. Soai, Angew. Chem. Int. Ed. 43 (2004) 4490–4492.
doi: 10.1002/anie.200454162
T. Kawasaki, M. Sato, S. Ishiguro, et al., J. Am. Chem. Soc. 127 (2005) 3274–3275.
doi: 10.1021/ja0422108
K. Soai, T. Kawasaki, A. Matsumoto, Acc. Chem. Res. 47 (2014) 3643–3654.
doi: 10.1021/ar5003208
K.P. Bryliakov, ACS Catal. 9 (2019) 5418–5438.
doi: 10.1021/acscatal.9b00697
Y. Geiger, T. Achard, A. Maisse-François, S. Bellemin-Laponnaz, Nat. Catal. 3 (2020) 422–426.
doi: 10.1038/s41929-020-0441-1
H.M. Dhammika Bandara, S.C. Burdette, Chem. Soc. Rev. 41 (2012) 1809–1825.
doi: 10.1039/C1CS15179G
P.K. Hashim, N. Tamaoki, ChemPhotoChem 3 (2019) 347–355.
doi: 10.1002/cptc.201900068
M. Mathews, N. Tamaoki, J. Am. Chem. Soc. 130 (2008) 11409–11416.
doi: 10.1021/ja802472t
P.K. Hashim, R. Thomas, N. Tamaoki, Chem. Eur. J. 17 (2011) 7304–7312.
doi: 10.1002/chem.201003526
G. Yang, Y.Y. Xu, Z.D. Zhang, et al., Chem. Commun. 53 (2017) 1735–1738.
doi: 10.1039/C6CC09256J
C.L. He, Z. Feng, Y. Li, et al., Polym. Chem. 12 (2021) 2433–2438.
doi: 10.1039/d1py00082a
M.M. Green, B.A. Garetz, B. Munoz, et al., J. Am. Chem. Soc. 117 (1995) 4181–4182.
doi: 10.1021/ja00119a039
J. Li, G.B. Schuster, K.S. Cheon, M.M. Green, J.V. Selinger, J. Am. Chem. Soc. 122 (2000) 2603–2612.
doi: 10.1021/ja993290w
L. Nikolova, T. Todorov, M. Ivanov, et al., Opt. Mater. 8 (1997) 255–258.
doi: 10.1016/S0925-3467(97)00046-3
L. Nikolova, L. Nedelchev, T. Todorov, et al., Appl. Phys. Lett. 77 (2000) 657–659.
doi: 10.1063/1.127076
S.W. Choi, S. Kawauchi, N.Y. Ha, H. Takezoe, Phys. Chem. Chem. Phys. 9 (2007) 3671–3682.
doi: 10.1039/b702835k
R.M. Tejedor, L. Oriol, J.L. Serrano, T. Sierra, J. Mater. Chem. 18 (2008) 2899–2908.
doi: 10.1039/b803561j
J. Royes, J. Rebolé, L. Custardoy, et al., J. Polym. Sci. Part A Polym. Chem. 50 (2012) 1579–1590.
doi: 10.1002/pola.25929
M. Fujiki, Y. Donguri, Y. Zhao, et al., Polym. Chem. 6 (2015) 1627–1638.
doi: 10.1039/C4PY01337A
L. Wang, L. Yin, W. Zhang, X. Zhu, M. Fujiki, J. Am. Chem. Soc. 139 (2017) 13218–13226.
doi: 10.1021/jacs.7b07626
C. Kulkarni, R.H.N. Curvers, G. Vantomme, et al., Adv. Mater. 33 (2021) 2005720.
doi: 10.1002/adma.202005720
Y. Wang, T. Sakamoto, T. Nakano, Chem. Commun. 48 (2012) 1871–1873.
doi: 10.1039/c2cc17027b
Y. Wang, T. Harada, L.Q. Phuong, Y. Kanemitsu, T. Nakano, Macromolecules 51 (2018) 6865–6877.
doi: 10.1021/acs.macromol.8b01453
Y. Wang, K. Yazawa, Q. Wang, et al., Chem. Commun. 57 (2021) 7681–7684.
doi: 10.1039/d1cc02671b
M. Liu, L. Zhang, T. Wang, Chem. Rev. 115 (2015) 7304–7397.
doi: 10.1021/cr500671p
J. Kim, J. Lee, W.Y. Kim, et al., Nat. Commun. 6 (2015) 6959.
doi: 10.1038/ncomms7959
J.S. Kang, S. Kang, J.M. Suh, et al., J. Am. Chem. Soc. 144 (2022) 2657–2666.
doi: 10.1021/jacs.1c11306
Z. Zhang, T. Harada, A. Pietropaolo, et al., Chem. Commun. 57 (2021) 1794–1797.
doi: 10.1039/d0cc07898k
Y. Wang, A.L. Kanibolotsky, P.J. Skabara, T. Nakano, Chem. Commun. 52 (2016) 1919–1922.
doi: 10.1039/C5CC08464D
W. Ma, L. Xu, A.F. de Moura, et al., Chem. Rev. 117 (2017) 8041–8093.
doi: 10.1021/acs.chemrev.6b00755
J. Liu, L. Yang, P. Qin, et al., Adv. Mater. 33 (2021) 2005506.
doi: 10.1002/adma.202005506
A. Passaseo, M. Esposito, M. Cuscunà, V. Tasco, Adv. Opt. Mater. 5 (2017) 1601079.
doi: 10.1002/adom.201601079
J. Yeom, B. Yeom, H. Chan, et al., Nat. Mater. 14 (2015) 66–72.
doi: 10.1038/nmat4125
H. Behar-Levy, O. Neumann, R. Naaman, D. Avnir, Adv. Mater. 19 (2007) 1207–1211.
doi: 10.1002/adma.200601702
J.Y. Kim, J. Yeom, G. Zhao, et al., J. Am. Chem. Soc. 141 (2019) 11739–11744.
doi: 10.1021/jacs.9b00700
L. Xu, X. Wang, W. Wang, et al., Nature 601 (2022) 366–373.
doi: 10.1038/s41586-021-04243-2
K. Wu, J. Chen, J.R. MeBride, T. Lian, Science 349 (2015) 632–635.
doi: 10.1126/science.aac5443
H. Tang, C.J. Chen, Z. Huang, et al., J. Chem. Phys. 152 (2020) 220901.
doi: 10.1063/5.0005334
K. Saito, T. Tatsuma, Nano Lett. 18 (2018) 3209–3212.
doi: 10.1021/acs.nanolett.8b00929
H. Wang, Y. Liu, J. Yu, et al., ACS Appl. Mater. Interfaces 14 (2022) 3559–3567.
doi: 10.1021/acsami.1c22191
Y. Tang, A.E. Cohen, Phys. Rev. Lett. 104 (2010) 163901.
doi: 10.1103/PhysRevLett.104.163901
Y. Tang, A.E. Cohen, Science 332 (2011) 333–336.
doi: 10.1126/science.1202817
N. Yang, Y. Tang, A.E. Cohen, Nano Today 4 (2009) 269–279.
doi: 10.1016/j.nantod.2009.05.001
N. Yang, A.E. Cohen, J. Phys. Chem. B 115 (2001) 5304–5311.
C. He, G. Yang, Y. Kuai, et al., Nat. Commun. 9 (2018) 5117.
doi: 10.1038/s41467-018-07533-y
K.S. Burnham, G.B. Schuster, J. Am. Chem. Soc. 121 (1999) 10245–10246.
doi: 10.1021/ja9923033
J. Yan, F. Ota, B.A. San Jose, K. Akagi, Adv. Funct. Mater. 27 (2017) 1604529.
doi: 10.1002/adfm.201604529
M. Zhang, Y. Wang, Y. Zhou, et al., Nanoscale 14 (2022) 592–601.
doi: 10.1039/d1nr06036h
N.A. Abdulrahman, Z. Fan, T. Tonooka, et al., Nano Lett. 12 (2012) 977–983.
doi: 10.1021/nl204055r
M. Schäferling, D. Dregely, M. Hentschel, H. Giessen, Phys. Rev. X 2 (2012) 031010.
doi: 10.1103/PhysRevX.2.031010
Y. Chen, W. Du, Q. Zhang, et al., Nat. Rev. Phys. 4 (2022) 113–124.
Wei X., Liu J., Xia G.J., et al. Nat. Chem. 12 (2020) 551–559.
doi: 10.1038/s41557-020-0453-0
Z.Y. Bao, W. Zhang, Y.L. Zhang, et al., Angew. Chem. Int. Ed. 56 (2017) 1283–1288.
doi: 10.1002/anie.201607563
K. Kolwas, A. Derkachova, Nanomaterials 10 (2020) 1411.
doi: 10.3390/nano10071411
C. He, Z. Feng, S. Shan, et al., Nat. Commun. 11 (2020) 1188.
doi: 10.1038/s41467-020-15082-6
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
Teng-Yu Huang , Junliang Sun , De-Xian Wang , Qi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758
Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
Qian Wang , Yeping Bian , Gagan Dhawan , Wei Zhang , Alexander E. Sorochinsky , Ata Makarem , Vadim A. Soloshonok , Jianlin Han . FDA approved fluorine-containing drugs in 2023. Chinese Chemical Letters, 2024, 35(11): 109780-. doi: 10.1016/j.cclet.2024.109780
Wenying Cui , Zhetong Jin , Wentao Fu , Chengshuo Shen . Flag-hinge-like highly luminescent chiral nanographenes with twist geometry. Chinese Chemical Letters, 2024, 35(11): 109667-. doi: 10.1016/j.cclet.2024.109667
Genlin Sun , Yachun Luo , Zhihong Yan , Hongdeng Qiu , Weiyang Tang . Chiral metal-organic frameworks-based materials for chromatographic enantioseparation. Chinese Chemical Letters, 2024, 35(12): 109787-. doi: 10.1016/j.cclet.2024.109787
Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M2L4 coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
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
Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
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
Yuanpeng Ye , Longfei Yao , Guofeng Liu . Engineering circularly polarized luminescence through symmetry manipulation in achiral tetraphenylpyrazine structures. Chinese Journal of Structural Chemistry, 2025, 44(2): 100460-100460. doi: 10.1016/j.cjsc.2024.100460
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
Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
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
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
Min-Hang Zhou , Jun Jiang , Wei-Min He . EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate. Chinese Chemical Letters, 2025, 36(1): 110446-. doi: 10.1016/j.cclet.2024.110446
Huashan Huang , Jingze Chen , Luyun Zhang , Hong Yan , Siqi Li , Fen-Er Chen . Oscillatory flow reactor facilitates fast photochemical Wolff rearrangement toward synthesis of α-substituted amides in flow. Chinese Chemical Letters, 2025, 36(2): 109992-. doi: 10.1016/j.cclet.2024.109992
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
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