Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 4039-4049.DOI: 10.6023/cjoc202105055 Previous Articles Next Articles
Special Issue: 南开大学化学学科创立100周年
ARTICLES
赵敏a, 李霏a, 程益政b, 王有名a, 周正洪a,*(
)
收稿日期:2021-05-31
修回日期:2021-06-22
发布日期:2021-07-05
通讯作者:
周正洪
Min Zhaoa, Fei Lia, Yizheng Chengb, Youming Wanga, Zhenghong Zhoua()
Received:2021-05-31
Revised:2021-06-22
Published:2021-07-05
Contact:
Zhenghong Zhou
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Min Zhao, Fei Li, Yizheng Cheng, Youming Wang, Zhenghong Zhou. Optically Active 3,4-Dihydrocoumarins via Organocatalyzed Asymmetric [4+2] Annulation of ortho-Hydroxyl Functionalized p-Quinone Methides with β-Keto Acylpyrazoles[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4039-4049.
| Entry | Catalyst | Time/h | Yieldb/% | Drc | eed/% |
|---|---|---|---|---|---|
| 1 | I | 8 | 81 | >19/1 | 77 |
| 2 | IIa | 12 | 89 | >19/1 | 67 |
| 3 | IIb | 12 | 85 | >19/1 | 70 |
| 4 | III | 8 | 90 | >19/1 | –89 |
| 5 | IV | 8 | 80 | >19/1 | 80 |
| 6 | Va | 12 | 84 | >19/1 | 78 |
| 7 | Vb | 12 | 83 | >19/1 | 76 |
| 8 | VIa | 8 | 89 | >19/1 | –77 |
| 9 | VIb | 8 | 86 | >19/1 | –79 |
| 10 | VIc | 8 | 79 | >19/1 | –83 |
| 11 | VII | 8 | 90 | >19/1 | –94 |
| Entry | Catalyst | Time/h | Yieldb/% | Drc | eed/% |
|---|---|---|---|---|---|
| 1 | I | 8 | 81 | >19/1 | 77 |
| 2 | IIa | 12 | 89 | >19/1 | 67 |
| 3 | IIb | 12 | 85 | >19/1 | 70 |
| 4 | III | 8 | 90 | >19/1 | –89 |
| 5 | IV | 8 | 80 | >19/1 | 80 |
| 6 | Va | 12 | 84 | >19/1 | 78 |
| 7 | Vb | 12 | 83 | >19/1 | 76 |
| 8 | VIa | 8 | 89 | >19/1 | –77 |
| 9 | VIb | 8 | 86 | >19/1 | –79 |
| 10 | VIc | 8 | 79 | >19/1 | –83 |
| 11 | VII | 8 | 90 | >19/1 | –94 |
| Entry | Solvent | Time/h | Yieldb/% | drc | eed/% |
|---|---|---|---|---|---|
| 1 | CH2Cl2 | 8 | 84 | >19/1 | 94 |
| 2 | CHCl3 | 8 | 80 | >19/1 | 88 |
| 3 | Cl(CH2)2Cl | 7 | 78 | >19/1 | 90 |
| 4 | PhCl | 6 | 79 | >19/1 | 84 |
| 5 | PhF | 6 | 75 | >19/1 | 80 |
| 6 | PhCH3 | 6 | 76 | >19/1 | 76 |
| 7 | EtOAc | 48 | 45 | >19/1 | 70 |
| 8 | CH3CN | 48 | 43 | >19/1 | 81 |
| 9e | CH2Cl2 | 36 | 80 | >19/1 | 93 |
| 10f | CH2Cl2 | 8 | 85 | >19/1 | 51 |
| 11g | CH2Cl2 | 5 | 80 | >19/1 | 88 |
| 12h | CH2Cl2 | 12 | 83 | >19/1 | 85 |
| Entry | Solvent | Time/h | Yieldb/% | drc | eed/% |
|---|---|---|---|---|---|
| 1 | CH2Cl2 | 8 | 84 | >19/1 | 94 |
| 2 | CHCl3 | 8 | 80 | >19/1 | 88 |
| 3 | Cl(CH2)2Cl | 7 | 78 | >19/1 | 90 |
| 4 | PhCl | 6 | 79 | >19/1 | 84 |
| 5 | PhF | 6 | 75 | >19/1 | 80 |
| 6 | PhCH3 | 6 | 76 | >19/1 | 76 |
| 7 | EtOAc | 48 | 45 | >19/1 | 70 |
| 8 | CH3CN | 48 | 43 | >19/1 | 81 |
| 9e | CH2Cl2 | 36 | 80 | >19/1 | 93 |
| 10f | CH2Cl2 | 8 | 85 | >19/1 | 51 |
| 11g | CH2Cl2 | 5 | 80 | >19/1 | 88 |
| 12h | CH2Cl2 | 12 | 83 | >19/1 | 85 |
| Entry | 3 (R, Ar) | Time/h | Yieldb/% | drc | eed/% |
|---|---|---|---|---|---|
| 1 | 3aa (H, Ph) | 8 | 84 | >19/1 | 94 |
| 2 | 3ba (4-Me, Ph) | 48 | 80 | >19/1 | 92 |
| 3 | 3ca (5-Me, Ph) | 48 | 81 | >19/1 | 97 |
| 4 | 3da (3-MeO, Ph) | 32 | 80 | >19/1 | 96 |
| 5 | 3ea (4-MeO, Ph) | 8 | 85 | >19/1 | 93 |
| 6 | 3fa (5-MeO, Ph) | 32 | 84 | >19/1 | 93 |
| 7 | 3ga (5-F, Ph) | 5 | 86 | >19/1 | 95 |
| 8 | 3ha (4-Cl, Ph) | 8 | 82 | >19/1 | 97 |
| 9 | 3ia (5-Cl, Ph) | 8 | 82 | >19/1 | 86 |
| 10 | 3ja (4-Br, Ph) | 8 | 77 | >19/1 | 98 |
| 11 | 3ka (5-Br, Ph) | 8 | 68 | >19/1 | 95 |
| 12 | 3ab (H, 4-MeC6H4) | 8 | 79 | >19/1 | 92 |
| 13 | 3ac (H, 3-MeC6H4) | 8 | 78 | >19/1 | 93 |
| 14 | 3ad (H, 2-MeC6H4) | 8 | 85 | >19/1 | 90 |
| 15 | 3ae (H, 4-MeOC6H4) | 8 | 85 | >19/1 | 91 |
| 16 | 3af (H, 3,4-(MeO)2C6H3) | 8 | 66 | >19/1 | 86 |
| 17 | 3ag (H, 4-FC6H4) | 8 | 83 | >19/1 | 93 |
| 18 | 3ah (H, 3-ClC6H4) | 8 | 90 | >19/1 | 96 |
| 19 | 3ai (H, 4-BrC6H4) | 8 | 81 | >19/1 | 94 |
| 20 | 3aj (H, 3-BrC6H4) | 8 | 80 | >19/1 | 95 |
| 21 | 3ak (H, 2-Naphthyl) | 8 | 89 | >19/1 | 87 |
| 22 | 3al (H, 2-Thienyl) | 8 | 90 | >19/1 | 93 |
| Entry | 3 (R, Ar) | Time/h | Yieldb/% | drc | eed/% |
|---|---|---|---|---|---|
| 1 | 3aa (H, Ph) | 8 | 84 | >19/1 | 94 |
| 2 | 3ba (4-Me, Ph) | 48 | 80 | >19/1 | 92 |
| 3 | 3ca (5-Me, Ph) | 48 | 81 | >19/1 | 97 |
| 4 | 3da (3-MeO, Ph) | 32 | 80 | >19/1 | 96 |
| 5 | 3ea (4-MeO, Ph) | 8 | 85 | >19/1 | 93 |
| 6 | 3fa (5-MeO, Ph) | 32 | 84 | >19/1 | 93 |
| 7 | 3ga (5-F, Ph) | 5 | 86 | >19/1 | 95 |
| 8 | 3ha (4-Cl, Ph) | 8 | 82 | >19/1 | 97 |
| 9 | 3ia (5-Cl, Ph) | 8 | 82 | >19/1 | 86 |
| 10 | 3ja (4-Br, Ph) | 8 | 77 | >19/1 | 98 |
| 11 | 3ka (5-Br, Ph) | 8 | 68 | >19/1 | 95 |
| 12 | 3ab (H, 4-MeC6H4) | 8 | 79 | >19/1 | 92 |
| 13 | 3ac (H, 3-MeC6H4) | 8 | 78 | >19/1 | 93 |
| 14 | 3ad (H, 2-MeC6H4) | 8 | 85 | >19/1 | 90 |
| 15 | 3ae (H, 4-MeOC6H4) | 8 | 85 | >19/1 | 91 |
| 16 | 3af (H, 3,4-(MeO)2C6H3) | 8 | 66 | >19/1 | 86 |
| 17 | 3ag (H, 4-FC6H4) | 8 | 83 | >19/1 | 93 |
| 18 | 3ah (H, 3-ClC6H4) | 8 | 90 | >19/1 | 96 |
| 19 | 3ai (H, 4-BrC6H4) | 8 | 81 | >19/1 | 94 |
| 20 | 3aj (H, 3-BrC6H4) | 8 | 80 | >19/1 | 95 |
| 21 | 3ak (H, 2-Naphthyl) | 8 | 89 | >19/1 | 87 |
| 22 | 3al (H, 2-Thienyl) | 8 | 90 | >19/1 | 93 |
| [1] |
(a) Asai, F.; Iinuma, M.; Tanaka, T.; Mizuno, M. Phytochemistry 1991, 30, 3091.
doi: 10.1016/S0031-9422(00)98259-1 pmid: 21315392 |
|
(b) Asai, F.; Iinuma, M.; Tanaka, T.; Mizuno, M. Heterocycles 1992, 33, 229.
doi: 10.3987/COM-91-S21 pmid: 21315392 |
|
|
(c) Asai, F.; Iinuma, M.; Tanaka, T.; Takenaka, M.; Mizuno, M. Phytochemistry 1992, 31, 2487.
doi: 10.1016/0031-9422(92)83306-J pmid: 21315392 |
|
|
(d) Ngadjui, B. T.; Kapche, G. W. F.; Tamboue, H.; Abegaz, B. M.; Connolly, J. D. Phytochemistry 1999, 51, 119.
doi: 10.1016/S0031-9422(98)00621-9 pmid: 21315392 |
|
|
(e) Seo, E.-K.; Wani, M. C.; Wall, M. E.; Navarro, H.; Mukherjee, R.; Farnsworth, N. R.; Kinghorn, A. D. Phytochemistry 2000, 55, 35.
pmid: 21315392 |
|
|
(f) Wu, P.-L.; Hsu, Y.-L.; Zao, C.-W.; Damu, A. G.; Wu, T.-S. J. Nat. Prod. 2005, 68, 1180.
doi: 10.1021/np050060o pmid: 21315392 |
|
|
(g) Wungsintaweekul, B.; Umehara, K.; Miyase, T.; Noguchi, H. Phytochemistry 2011, 72, 495.
doi: 10.1016/j.phytochem.2010.12.018 pmid: 21315392 |
|
|
(h) Ee, G. C. L.; Mah, S. H.; The, S. S.; Rahmani, M.; Go, R.; Taufiq-Yap, Y. H. Molecules 2011, 16, 9721.
doi: 10.3390/molecules16119721 pmid: 21315392 |
|
| [2] |
For selected examples, see: (a) Bedalov, A.; Gatbonton, T.; Irvine, W. P.; Gottschling, D. E.; Simon, J. A. Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 15113.
pmid: 23354072 |
|
(b) Posakony, J.; Hirao, M.; Stevens, S.; Simon, J. A.; Bedalov, A. J. Med. Chem. 2004, 47, 2635.
pmid: 23354072 |
|
|
(c) Roelens, F.; Huvaere, K.; Dhooge, W.; Van Cleemput, M.; Comhaire, F.; de Keukeleire, D. Eur. J. Med. Chem. 2005, 40, 1042.
doi: 10.1016/j.ejmech.2005.04.010 pmid: 23354072 |
|
|
(d) Zhang, X.; Wang, H.; Song, Y.; Nie, L.; Wang, L.; Liu, B.; Shen, P.; Liu, Y. Bioorg. Med. Chem. Lett. 2006, 16, 949.
doi: 10.1016/j.bmcl.2005.10.096 pmid: 23354072 |
|
|
(e) Modranka, J.; Albrecht, A.; Jakubowski, R.; Krawczyk, H.; Roóżalski, M.; Krajewska, U.; Janecka, A.; Wyrębska, A.; Różalska, B.; Janecki, T. Bioorg. Med. Chem. 2012, 20, 5017.
doi: 10.1016/j.bmc.2012.06.022 pmid: 23354072 |
|
|
(f) Sashidhara, K. V.; Singh, S. P.; Singh, S. V.; Srivastava, R. K.; Srivastava, K.; Saxena, J. K.; Puri, S. K. Eur. J. Med. Chem. 2013, 60, 497.
doi: 10.1016/j.ejmech.2012.12.019 pmid: 23354072 |
|
|
(g) Zhang, K.; Ding, W.; Sun, J.; Zhang, B.; Lu, F.; Lai, R.; Zou, Y.; Yedid, G. Biochimie 2014, 107, 203.
doi: 10.1016/j.biochi.2014.03.014 pmid: 23354072 |
|
|
(h) Deredas, D.; Huben, K.; Janecka, A.; Długosz, A.; Pomorska, D. K.; Mirowski, M.; Krajewska, U.; Janeckia, T.; Krawczyk, H. MedChemComm 2016, 7, 1745.
doi: 10.1039/C6MD00118A pmid: 23354072 |
|
| [3] |
(a) Song, F.; Lu, S.; Gunnet, J.; Xu, J. Z.; Wines, P.; Proost, J.; Liang, Y.; Baumann, C.; Lenhard, J.; Murray, W. V.; Demarest, K. T.; Kuo, G.-H. J. Med. Chem. 2007, 50, 2807.
doi: 10.1021/jm070130j pmid: 19402693 |
|
(b) Ballerini, E.; Minuti, L.; Piermatti, O.; Pizzo, F. J. Org. Chem. 2009, 74, 4311.
doi: 10.1021/jo9005365 pmid: 19402693 |
|
| [4] |
For a review on the asymmetric construction of 3,4-dihydrocoumarins, see: Leitis, Z. Chem. Heterocycl. Compd. 2016, 52, 527.
doi: 10.1007/s10593-016-1922-7 |
| [5] |
(a) Alden-Danforth, E.; Scerba, M. T.; Lectka, T. Org. Lett. 2008, 10, 4951.
doi: 10.1021/ol802029e pmid: 26990670 |
|
(b) Lü, H.; You, L.; Ye, S. Adv. Synth. Catal. 2009, 351, 2822.
doi: 10.1002/adsc.v351:17 pmid: 26990670 |
|
|
(c) Izquierdo, J.; Orue, A.; Scheidt, K. A. J. Am. Chem. Soc. 2013, 135, 10634.
doi: 10.1021/ja405833m pmid: 26990670 |
|
|
(d) Lee, A.; Scheidt, K. A. Chem. Commun. 2015, 51, 3407.
doi: 10.1039/C4CC09590A pmid: 26990670 |
|
|
(e) Caruana, L.; Mondatori, M.; Corti, V.; Morales, S.; Mazzanti, A.; Fochi, M.; Bernardi, L. Chem.-Eur. J. 2015, 21, 6037.
doi: 10.1002/chem.v21.16 pmid: 26990670 |
|
|
(f) Zhou, D.; Mao, K.; Zhang, J.; Yan, B.; Wang, W.; Xie, H. Tetrahedron Lett. 2016, 57, 5649.
pmid: 26990670 |
|
|
(g) Yu, X.-Y.; Chen, J.-R.; Wei, Q.; Cheng, H.-G.; Liu, Z.-C.; Xiao, W.-J. Chem.-Eur. J. 2016, 22, 6774.
doi: 10.1002/chem.201601227 pmid: 26990670 |
|
|
(h) Zhang, Y.-C.; Zhu, Q.-N.; Yang, X.; Zhou, L.-J.; Shi, F. J. Org. Chem. 2016, 81, 1681.
doi: 10.1021/acs.joc.6b00078 pmid: 26990670 |
|
|
(i) Jin, J.-H.; Li, X.-Y.; Luo, X.; Fossey, J. S.; Deng, W.-P. J. Org. Chem. 2017, 82, 5424.
doi: 10.1021/acs.joc.7b00367 pmid: 26990670 |
|
|
(j) Wu, B.; Yu, Z.; Gao, X.; Lan, Y.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2017, 56, 4006.
doi: 10.1002/anie.201700437 pmid: 26990670 |
|
|
(k) Chen, X.; Song, R.; Liu, Y.; Ooi, C. Y.; Jin, Z.; Zhu, T.; Wang, H.; Hao, L.; Chi, Y. R. Org. Lett. 2017, 19, 5892;
doi: 10.1021/acs.orglett.7b02883 pmid: 26990670 |
|
|
(l) Zhang, T.; Ma, C.; Zhou, J.-Y.; Mei, G.-J.; Shi, F. Adv. Synth. Catal. 2018, 360, 1128.
doi: 10.1002/adsc.v360.6 pmid: 26990670 |
|
|
(m) Alden-Danforth, E.; Scerba, M. T.; Lectka, T. Org. Lett. 2018, 10, 4951.
doi: 10.1021/ol802029e pmid: 26990670 |
|
|
(n) Cui, L.; Lv, D.; Wang, Y.; Fan, Z.; Li, Z.; Zhou, Z. J. Org. Chem. 2018, 82, 4221.
pmid: 26990670 |
|
|
(o) Lv, D.; Zhao, M.; Wang, Y.; Zhou, Z. Org. Biomol. Chem. 2019, 17, 9636.
doi: 10.1039/C9OB02089F pmid: 26990670 |
|
|
(p) Kim, K. S.; Jang, J.; Kim, D. Y. ChemistrySelect 2020, 5, 13259.
doi: 10.1002/slct.v5.42 pmid: 26990670 |
|
| [6] |
For selected reviews on p-QMs, see: (a) Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733.
doi: 10.3390/molecules200711733 |
|
(b) Parra, A.; Tortosa, M. ChemCatChem 2015, 7, 1524.
doi: 10.1002/cctc.v7.10 |
|
|
(c) Chauhan, P.; Kaya, U.; Enders, D. Adv. Synth. Catal. 2017, 359, 888.
doi: 10.1002/adsc.201601342 |
|
|
(d) Lima, C. G. S.; Pauli, F. P.; Costa, D. C. S.; de Souza, A. S.; Ferreira, V. F.; de Carvalho da Silva, F. Eur. J. Org. Chem. 2020, 2650.
|
|
|
(e) Wang, J.-Y.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Org. Chem. Front. 2020, 7, 1743.
doi: 10.1039/D0QO00387E |
|
| [7] |
Zhao, K.; Zhi, Y.; Shu, T.; Valkonen, A.; Rissanen, K.; Enders, D. Angew. Chem., Int. Ed. 2016, 55, 12104.
doi: 10.1002/anie.201606947 |
| [8] |
(a) Liu, L.; Yuan, Z.; Pan, R.; Zeng, Y.; Lin, A.; Yao, H.; Huang, Y. Org. Chem. Front. 2018, 5, 623.
doi: 10.1039/C7QO00846E pmid: 31490078 |
|
(b) Zielke, K.; Kováč, O.; Winter, M.; Pospíšil, J.; Waser, M. Chem.-Eur. J. 2019, 25, 8163.
doi: 10.1002/chem.v25.34 pmid: 31490078 |
|
|
(c) Tan, J.-P.; Yu, P.; Wu, J.-H.; Chen, Y.; Pan, J.; Jiang, C.; Ren, X.; Zhang, H.-S.; Wang, T. Org. Lett. 2019, 21, 7298.
doi: 10.1021/acs.orglett.9b02560 pmid: 31490078 |
|
|
(d) Lu, H.; Zhang, H.-X.; Tan, C.-Y.; Liu, J.-Y.; Wei, H.; Xu, P.-F. J. Org. Chem. 2019, 84, 10292.
doi: 10.1021/acs.joc.9b01454 pmid: 31490078 |
|
| [9] |
(a) Zhang, L.; Zhou, X.; Li, P.; Liu, Z.; Liu, Y.; Sun, Y.; Li, W. RSC Adv. 2017, 7, 39216.
doi: 10.1039/C7RA08157J pmid: 28991314 |
|
(b) Zhang, L.; Liu, Y.; Liu, K.; Liu, Z.; He, N.; Li, W. Org. Biomol. Chem. 2017, 15, 8743.
doi: 10.1039/c7ob02325a pmid: 28991314 |
|
|
(c) Duan, C.; Ye, L.; Xu, W.; Li, X.; Chen, F.; Zhao, Z.; Li, X. Chin. Chem. Lett. 2018, 29, 1273.
doi: 10.1016/j.cclet.2017.11.044 pmid: 28991314 |
|
|
(d) Zhang, Z.-P.; Xie, K.-X.; Yang, C.; Li, M.; Li, X. J. Org. Chem. 2018, 83, 364.
doi: 10.1021/acs.joc.7b02750 pmid: 28991314 |
|
|
(e) Zhang, Z.-P.; Chen, L.; Li, X.; Cheng, J.-P. J. Org. Chem. 2018, 83, 2714.
doi: 10.1021/acs.joc.7b03177 pmid: 28991314 |
|
|
(f) Jiang, X.-L.; Wu, S.-F.; Wang, J.-R.; Mei, G.-J.; Shi, F. Adv. Synth. Catal. 2018, 360, 4225.
doi: 10.1002/adsc.v360.21 pmid: 28991314 |
|
|
(g) Yang, G.-H.; Zhao, Q.; Zhang, Z.-P.; Zheng, H.-L.; Chen, L.; Li, X. J. Org. Chem. 2019, 84, 7883.
doi: 10.1021/acs.joc.9b00749 pmid: 28991314 |
|
|
(h) You, Y.; Li, T.-T.; Yuan, S.-P.; Xie, K.-X.; Wang, Z.-H.; Zhao, J.-Q.; Zhou, M.-Q.; Yuan, W.-C. Chem. Commun. 2020, 56, 439.
doi: 10.1039/C9CC08316B pmid: 28991314 |
|
|
(i) Tan, J.-P.; Zhang, H.; Jiang, Z.; Chen, Y.; Ren, X.; Jiang, C.; Wang, T. Adv. Synth. Catal. 2020, 362, 1058.
doi: 10.1002/adsc.201901413 pmid: 28991314 |
|
|
(j) Zhao, M.-X.; Xiang, J.; Zhao, Z.-Q.; Zhao, X.-L.; Shi, M. Org. Biomol. Chem. 2020, 18, 1637.
doi: 10.1039/C9OB02652E pmid: 28991314 |
|
|
(k) Roy, S.; Pradhan, S.; Kumar, K.; Chatterjee, I. Org. Chem. Front. 2020, 7, 1388.
doi: 10.1039/D0QO00354A pmid: 28991314 |
|
|
(l) Wu, S.-F.; Tu, M.-S.; Hang, Q.-Q.; Zhang, S.; Ding, H.; Zhang, Y.-C.; Shi, F. Org. Biomol. Chem. 2020, 18, 5388.
doi: 10.1039/D0OB01049A pmid: 28991314 |
|
|
(m) Xiang, M.; Li, C.-Y.; Song, X.-J.; Zou, Y.; Huang, Z.-C.; Li, X.; Tian, F.; Wang, L.-X. Chem. Commun. 2020, 56, 14825.
doi: 10.1039/D0CC06777F pmid: 28991314 |
|
| [10] |
(a) Li, W.; Yuan, H.; Liu, Z.; Zhang, Z.; Cheng, Y.; Li, P. Adv. Synth. Catal. 2018, 360, 2460.
doi: 10.1002/adsc.v360.13 |
|
(b) Liu, Q.; Li, S.; Chen, X.-Y.; Rissanen, K.; Enders, D. Org. Lett. 2018, 20, 3622.
doi: 10.1021/acs.orglett.8b01400 |
|
|
(c) Jiang, F.; Yuan, F.-R.; Jin, L.-W.; Mei, G.-J.; Shi, F. ACS Catal. 2018, 8, 10234.
doi: 10.1021/acscatal.8b03410 |
|
|
(d) Sun, M.; Ma, C.; Zhou, S.-J.; Lou, S.-F.; Xiao, J.; Jiao, Y.; Shi, F. Angew. Chem., Int. Ed. 2019, 58, 8703.
doi: 10.1002/anie.v58.26 |
|
| [11] |
(a) Xiao, Y.; Wang, Y.; Zhou, Z. Chin. J. Org. Chem. 2019, 39, 2203. (in Chinese)
doi: 10.6023/cjoc201703070 pmid: 27100356 |
|
(肖园园, 王有名, 周正洪, 有机化学, 2019, 39, 2203.)
doi: 10.6023/cjoc201703070 pmid: 27100356 |
|
|
(b) Xiao, Y.; Jiang, R.; Wang, Y.; Zhou, Z. Adv. Synth. Catal. 2018, 360, 1961.
doi: 10.1002/adsc.v360.10 pmid: 27100356 |
|
|
(c) Zhang, H.; Wang, Y.; Zhou, Z. Tetrahedron 2018, 74, 6071.
doi: 10.1016/j.tet.2018.08.052 pmid: 27100356 |
|
|
(d) Chen, S.; Wang, Y.; Zhou, Z. J. Org. Chem. 2016, 81, 11432.
doi: 10.1021/acs.joc.6b02070 pmid: 27100356 |
|
|
(e) Zheng, Y.; Cui, L.; Wang, Y.; Zhou, Z. J. Org. Chem. 2016, 81, 4340.
doi: 10.1021/acs.joc.6b00196 pmid: 27100356 |
|
|
(f) Wang, Y.; Pan, J.; Jiang, R.; Wang, Y.; Zhou, Z. Adv. Synth. Catal. 2016, 358, 195.
doi: 10.1002/adsc.v358.2 pmid: 27100356 |
|
|
(g) Zheng, Y.; Wang, Y.; Zhou, Z. Chem. Commun. 2015, 51, 11652.
pmid: 27100356 |
|
|
(h) Wu, L.; Wang, Y.; Song, H.; Tang, L.; Zhou, Z.; Tang, C. ChemCatChem 2014, 6, 649.
doi: 10.1002/cctc.v6.2 pmid: 27100356 |
|
|
(i) Wu, L.; Wang, Y.; Song, H.; Tang, L.; Zhou, Z.; Tang, C. Chem. Asian J. 2013, 8, 2204.
doi: 10.1002/asia.201300450 pmid: 27100356 |
|
|
(j) Wu, L.; Wang, Y.; Song, H.; Tang, L.; Zhou, Z.; Tang, C. Adv. Synth. Catal. 2013, 355, 1053.
doi: 10.1002/adsc.v355.6 pmid: 27100356 |
|
|
(k) Lu, A.; Hu, K.; Wang, Y.; Song, H.; Zhou, Z.; Fang, J.; Tang, C. J. Org. Chem. 2012, 77, 6208.
doi: 10.1021/jo301006e pmid: 27100356 |
|
| [12] |
CCDC-2086168 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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