Enantioselective Synthesis of Atropisomers Featuring Pentatomic Heteroaromatics
- Corresponding author: Shi Bingfeng, bfshi@zju.edu.cn
Citation:
Zhang Shuo, Liao Gang, Shi Bingfeng. Enantioselective Synthesis of Atropisomers Featuring Pentatomic Heteroaromatics[J]. Chinese Journal of Organic Chemistry,
;2019, 39(6): 1522-1528.
doi:
10.6023/cjoc201904030
(a) Smyth, J. E.; Butler, N. M.; Keller, P. A. Nat. Prod. Rep. 2015, 32, 1562.
(b) Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563.
(c) LaPlante, S. R.; Fader, L. D.; Fandrick, K. R.; Fandrick, D. R.; Hucke, O.; Kemper, R.; Miller, S. P. F.; Edwards, P. J. J. Med. Chem. 2011, 54, 7005.
(d) Clayden, J.; Moran, W. J.; Edwards, P. J.; LaPlante, S. R. Angew. Chem., Int. Ed. 2009, 48, 6398.
(e) Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193;
(a) Baudoin, O. Eur. J. Org. Chem. 2005, 4223.
(b) Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
(c) Wallace, T. W. Org. Biomol. Chem. 2006, 4, 3197.
(d) Bringmann, G.; Menche, D. Acc. Chem. Res. 2011, 34, 615.
(e) Wencel-Delord, J.; Panossian, A; Leroux, F. R.; Colobert, F. Chem. Soc. Rev. 2015, 44, 3418.
(f) Ma, G.; Sibi, M. P. Chem.-Eur. J. 2015, 21, 11644.
(g) Kumarasamy, E.; Raghunathan, R.; Sibi, M. P.; Sivaguru, J. Chem. Rev. 2015, 115, 11239.
(h) Loxq, P.; Manoury, E.; Poli, R.; Deydier, E.; Labande, A. Coord. Chem. Rev. 2016, 308, 131.
(i) Mori, K.; Itakura, T.; Akiyama, T. Angew. Chem., Int. Ed. 2016, 55, 11642.
(j) Xu, C.; Zheng, H.; Hu, B.; Liu, X.; Liu, L.; Feng, X. Chem. Commun. 2017, 53, 9741.
(k) Zilate, B.; Castrogiovanni, A.; Sparr, C. ACS Catal. 2018, 8, 2981.
(l) Link, A.; Sparr, C. Chem. Soc. Rev. 2018, 47, 3804. (m) Wang, Y.-B.; Tan, B. Acc. Chem. Res. 2018, 51, 534.
(a) Bonne, D.; Rodriguez, J. Eur. J. Org. Chem. 2018, 2417.
(b) Bonne, D.; Rodriguez, J. Chem. Commun. 2017, 53, 12385.
(a) Alkorta, I.; Elguero, J.; Roussel, C.; Vanthuyne, N.; Piras, P. Adv. Heterocycl. Chem. 2012, 105, 1.
(b) Djafri, A.; Roussel, C.; Sandströ m, J. J. Chem. Soc., Perkin Trans. 2 1985, 273.
(c) Lomas, J. C.; Lacroix, J.-C.; Vaisser-mann, J. J. Chem. Soc., Perkin Trans. 2 1999, 2001.
(d) Benincori, T.; Brenna, E.; Sannicolo, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E. J. Chem. Soc., Chem. Commun. 1995, 685.
Oki, M. Top. Stereochem. 1983, 14, 1.
Norton, R. S.; R. Wells, J. J. Am. Chem. Soc. 1982, 104, 3628.
doi: 10.1021/ja00377a014
Ito, C.; Thoyama, Y.; Omura, M.; Kjiura, I.; Furukawa, H. Chem. Pharm. Bull. 1993, 41, 2096
doi: 10.1248/cpb.41.2096
(a) Hughes, C. C.; Pietro-Davo, A.; Jensen, P. R.; Fenical, W. Org. Lett. 2008, 10, 629.
(b) Schneider, P.; Schneider, G. Chem. Commun. 2017, 53, 2272.
(c) Cheng, C.; Pan, L.; Chen, Y.; Song, H.; Qin, Y.; Li, R. J. Comb. Chem. 2010, 12, 541.
(d) Kanakis, A. A.; Sarli, V. Org. Lett. 2010, 12, 4872.
(a) Urban, S.; Hobbs, L.; Hooper, J. N. A.; Capon, R. J. Aust. J. Chem. 1995, 48, 1491.
(b) De Silva, K. T.; Ratcliffe, A. H.; Smith, G. F.; Smith, G. N. Tetrahedron Lett. 1972, 13, 913.
Schneiderab, P.; Schneider, G. Chem. Commun. 2017, 53, 2272.
doi: 10.1039/C6CC09693J
(a) Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E. J. Chem. Soc., Chem. Commun. 1995, 685.
(b) Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. J. Org. Chem. 1996, 61, 6244.
(c) Benincori, T.; Cesarotti, E.; Piccolo, O.; Sannicolò, F. J. Org. Chem. 2000, 65, 2043.
(d) Andersen, N.; Parvez, M.; Keay, B. A. Org. Lett. 2000, 2, 2817.
(a) Yamaguchi, K.; Yamaguchi, J.; Studer, A.; Itami, K. Chem. Sci. 2012, 3, 2165.
(b) Yamaguchi, K.; Kondo, H.; Yamaguchi, J.; Itami, K. Chem. Sci. 2013, 4, 3753.
Zhang, H.-H.; Wang, C.-S.; Li, C.; Mei, G.-J.; Li, Y.; Shi, F. Angew. Chem., Int. Ed. 2017, 56, 116.
doi: 10.1002/anie.201608150
Ma, C.; Jiang, F.; Sheng, F.-T.; Jiao, Y.; Mei, G.-J.; Shi, F. Angew. Chem. Int. Ed. 2019, 58, 3014.
doi: 10.1002/anie.201811177
Zhang, L.; Zhang, J.; Ma, J.; Cheng, D.-J.; Tan, B. J. Am. Chem. Soc. 2017, 139, 1714.
doi: 10.1021/jacs.6b09634
Raut, V. S.; Jean, M.; Vanthuyne, N.; Roussel, C.; Constantieux, T.; Bressy, C.; Bugaut, X.; Bonne, D.; Rodriguez, J. J. Am. Chem. Soc. 2017, 139, 2140.
doi: 10.1021/jacs.6b11079
Wang, D.; Tong, X. Org. Lett. 2017, 19, 6392.
doi: 10.1021/acs.orglett.7b03250
Link, A.; Sparr, C. Angew. Chem. Int. Ed. 2018, 57, 7136.
doi: 10.1002/anie.v57.24
Qi, L.-W.; Mao, J.-H.; Zhang, J.; Tan, B. Nat. Chem. 2018, 10, 58.
doi: 10.1038/nchem.2866
He, C.; Hou, M.; Zhu, Z.; Gu, Z. ACS Catal. 2017, 7, 5316.
doi: 10.1021/acscatal.7b01855
(a) Ototake, N.; Morimoto, Y.; Mokuya, A.; Fukaya, H.; Shida, Y.; Kitagawa, O. Chem.-Eur. J. 2010, 16, 6752.
(b) Peng, C.; Kusakabe, T.; Kikkawa, S.; Mochida, T.; Azumaya, I.; DaulatDhage, Y.; Takahashi, K.; Sasai, H.; Kato, K. Chem.-Eur. J. 2019, 25, 733.
Zhang, S.; Yao, Q.-J.; Liao, G.; Li, X.; Li, H.; Chen, H.-M.; Hong, X.; Shi, B.-F. ACS Catal. 2019, 9, 1956.
doi: 10.1021/acscatal.8b04870
Li, T.-R.; Zhang, M.-M.; Wang, B.-C.; Lu, L.-Q.; Xiao, W.-J. Org. Lett. 2018, 20, 3237.
doi: 10.1021/acs.orglett.8b01100
Zheng, S.-C.; Wang, Q.; Zhu, J. Angew. Chem. Int. Ed. 2019, 58, 1494.
doi: 10.1002/anie.201812654
(a) Zhang, F.-L.; Hong, K.; Li, T.-J.; Park, H.; Yu, J.-Q. Science 2016, 351, 252.
(b) Park, H.; Verma, P.; Hong, K.; Yu, J.-Q. Nat. Chem. 2018, 10, 755.
(a) Yao, Q.-J.; Zhang, S.; Zhan, B.-B.; Shi, B.-F. Angew. Chem., Int. Ed. 2017, 56, 6617.
(b) Liao, G.; Yao, Q.-J.; Zhang, Z.-Z.; Wu, Y.-J.; Huang, D.-Y.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, 57, 3661.
(c) Liao, G.; Li, B.; Chen, H.-M.; Yao, Q.-J.; Xia, Y.-N.; Luo, J.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, 57, 17151.
He, X.-L.; Zhao, H.-R.; Song, X.; Jiang, B.; Du, W.; Chen, Y.-C. ACS Catal. 2019, 9, 4374.
doi: 10.1021/acscatal.9b00767
Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
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
Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
.
CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
. CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050