SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 5: 1535 - 1548

DOI: https://doi.org/10.6023/cjoc202311002

ARTICLES

cis-Selective [5＋2]-Cycloaddition Reactions of Cyclic Morita-Baylis- Hillman Alcohols and Its Analogues with Arylethylenes Catalyzed by Ag(I)

  • Yongwei Cui ,
  • Chunmiao Liang ,
  • Haitao Zhu ,
  • Chengping Shen ,
  • Feiyang Ren ,
  • Menghan Sun ,
  • Yuan Zhao ,
  • Wenjing Wang ,
  • Dongmei Wang ,
  • Nini Zhou
Expand
  • College of Chemistry and Chemical Engineering, Shannxi Key Laboratory of Phytochemistry, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013
*E-mail: ;
;

Received date: 2023-11-02

  Revised date: 2024-01-17

  Online published: 2024-02-07

Supported by

Natural Science Foundation of Shaanxi Province(2021JQ-802); Scientific Research Program Funded by Shaanxi Provincial Education Department(21JK0476); Innovation Capability Support Program of Shaanxi Province(2022TD-63); Innovation R&D Team of BUAS on Qinling Medicinal Plants and Functional Organic Molecules

Fold

Abstract

An AgSbF6-catalyzed diastereoselective [5＋2]-cycloaddition reaction was developed as an efficient entry into indanone-fused benzo[7]annulene frameworks from cyclic Morita-Baylis-Hillman alcohols and its analogues with aryl- ethylenes. Density functional theory (DFT) calculation data analysis shows that 1,3-cis-selectivity might be mainly controlled by kinetics. The resulting dihydrodibenzo[a,f]azulen-12-one 3a can be further functionalized by using the regioselective hydrogenation and cyclopropanation.

Key words： Morita-Baylis-Hillman alcohol; arylethylenes; silver catalysis; [5＋2]-cycloaddition

Cite this article

Yongwei Cui , Chunmiao Liang , Haitao Zhu , Chengping Shen , Feiyang Ren , Menghan Sun , Yuan Zhao , Wenjing Wang , Dongmei Wang , Nini Zhou . cis-Selective [5＋2]-Cycloaddition Reactions of Cyclic Morita-Baylis- Hillman Alcohols and Its Analogues with Arylethylenes Catalyzed by Ag(I)[J]. Chinese Journal of Organic Chemistry, 2024 , 44(5) : 1535 -1548 . DOI: 10.6023/cjoc202311002

References

[1]
(a) Zheng, S. Q.; Lu, X. Y. Org. Lett. 2009, 11, 3978.
[1]
(b) Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1.
[1]
(c) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447.
[1]
(d) Ojha, D. P.; Prabhu, K. R. Org. Lett. 2015, 17, 4490.
[1]
(e) Guo, H. C.; Fan, Y. C.; Sun, Z. H.; Wu, Y.; Kwon, O. Chem. Rev. 2018, 118, 10049.
[1]
(f) Zhong, Y.; Zhao, X. Y.; Gan, L.; Hong, S. H.; Jiang, X. X. Org. Lett. 2018, 20, 4250.
[1]
(g) Wang, Y.; Jia, S. M.; Li, E. Q.; Duan, Z. J. Org. Chem. 2019, 84, 15323.
[1]
(h) Meng, Z. R.; Wang, Q. Q.; Lu, D. D.; Yue, T. T.; Ai, P.; Liu, H.; Yang, W. R.; Zheng, J. J. Org. Chem. 2020, 85, 15026.
[1]
(i) Lu, Z. Y.; Jia, Y. W.; Chen, X. L.; Li, P. F. J. Org. Chem. 2022, 87, 3184.
[1]
(j) He, Y. L.; Cai, W.; Huang, Y. Org. Lett. 2023, 25, 3347.
[1]
(k) Bhattacharyya, H.; Saha, S. J.; Verma, K.; Punniyamurthy, T. L. Org. Lett. 2023, 25, 6830.
[2]
(a) Martínez, I.; Andrews, A. E.; Emch, J. D.; Ndakala, A. J.; Wang, J.; Howell, A. R. Org. Lett. 2003, 5, 399.
[2]
(b) Linstadt, R. T. H.; Peterson, C. A.; Jette, C. I.; Boskovic, Z. V.; Lipshutz, B. H. Org. Lett. 2017, 19, 328.
[2]
(c) Mantovani, S.; Pintus, A.; Kovtun, A.; Bertuzzi, G.; Melucci, M.; Bandini, M. Eur. J. Org. Chem. 2023, 26, e202300641.
[3]
(a) Wu, C.; Zeng, H.; Liu, Z.; Liu, L.; Wang, D.; Chen, Y. J. Chin. J. Chem. 2011, 29, 2732.
[3]
(b) Li, Y. X.; Xuan, Q. Q.; Liu, L.; Wang, D.; Chen, Y. J.; Li, C. J. J. Am. Chem. Soc. 2013, 135, 12536.
[4]
Cai, X.; Xing, H.; Qiu, J.; Li, B.; Xie, P. Org. Lett. 2021, 23, 4368.
[5]
(a) Gendrineau, T.; Genet, J. P.; Darses, S. Org. Lett. 2010, 12, 308.
[5]
(b) Wang, Y.; Feng, X.; Du, H. Org. Lett. 2011, 13, 4954.
[5]
(c) Wang, F.; Li, S.; Qu, M.; Zhao, M. X.; Liu, L. J.; Shi, M. Chem. Commun. 2011, 47, 12813.
[6]
Zhang, X. X.; Rao, W. D.; Sally; Chan, P. W. H. Org. Biomol. Chem. 2009, 7, 4186.
[7]
Piao, C. R.; Zhao, Y. L.; Han, X. D.; Liu, Q. J. Org. Chem. 2008, 73, 2264.
[8]
Xie, P.; Li, S.; Liu, Y.; Cai, X.; Wang, J.; Yang, X.; Loh, T. P. Org. Lett. 2020, 22, 31.
[9]
Xie, P. Z.; Wang, J. Y.; Fan, J.; Liu, Y. N.; Wo, X. Y.; Loh, T. P. Green Chem. 2017, 19, 2135.
[10]
(a) Olomola, T. O.; Klein, P.; Caira, M. R.; Kaye, P. T. J. Org. Chem. 2016, 81, 109.
[10]
(b) Takizawa, S. B.; Arteaga, F. A.; Kishi, K.; Hirata, S. C.; Sasai, H. Org. Lett. 2014, 16, 4162.
[10]
(c) Wu, C.; Liu, Y. L.; Zeng, H.; Liu, L.; Wang, D.; Chen, Y. J. Org. Biomol. Chem. 2011, 9, 253.
[10]
(d) Xuan, Q. Q.; Zhong, N. J.; Ren, C. L.; Liu, L.; Wang, D.; Chen, Y. J.; Li, C. J. J. Org. Chem. 2013, 78, 11076.
[10]
(e) Lorion, M. M.; Gasperini, D.; Oble, J. L.; Poli, G. Org. Lett. 2013, 15, 3050.
[11]
(a) Qiao, Z.; Shafiq, Z.; Liu, L.; Yu, Z. B.; Zheng, Q. Y.; Wang, D.; Chen, Y. J. Angew. Chem., Int. Ed. 2010, 49, 7294.
[11]
(b) Qiao, Z.; Zhong, N. J.; Zhang, T.; Liu, L.; Wang, D.; Chen, Y. J. Eur. J. Org. Chem. 2013, 2013, 2140.
[12]
Basavaiah, D.; Srivardhana, J. S.; Reddy, R. J. J. Org. Chem. 2004, 69, 7379.
[13]
Janreddy, D.; Kavala, V. B.; Kotipalli, T.; Rajawinslin, R. R.; Kuo, C. W.; Huanga, W. C.; Yao, C. F. Org. Biomol. Chem. 2014, 12, 8247.
[14]
Sruthi, P. R.; Saranya, T. V.; Anas, S. ChemistrySelect 2020, 5, 1648.
[15]
Reddy, C. R.; Warudikar, K. K.; Sridhar, B. B. ACS Omega 2018, 3, 15734.
[16]
Reddy, C. R.; Patil, A. D. Org. Lett. 2021, 23, 4749.
[17]
Yang, H. T.; Ren, W. L.; Miao, C. B.; Dong, C. P.; Yang, Y.; Xi, H. T.; Meng, Q.; Jiang, Y.; Sun, X. Q. J. Org. Chem. 2013, 78, 1163.
[18]
Zhou, L. J.; Yuan, C. H.; Zeng, Y.; Wang, Q. J.; Wang, C.; Liu, M.; Wang, W.; Wu, Y. J.; Zheng, B.; Guo, H. C. Org. Lett. 2019, 21, 4882.
[19]
Stiller, J. L.; Kowalczyk, D.; Jiang, H.; J?rgensen, K. A.; Albrecht, L. Chem.-Eur. J. 2014, 20, 13108.
[20]
Ren, C. L.; Wei, F.; Xuan, Q. Q.; Wang, D.; Liu, L. Adv. Synth. Catal. 2016, 358, 132.
[21]
Yang, Q. Q.; Yin, X.; He, X. L.; Du, W.; Chen, Y. C. ACS Catal. 2019, 9, 1258.
[22]
(a) Tan, W.; Zhang, J. Y.; Cao, C. H.; Shi, F. Sci. China: Chem. 2023, 66, 966.
[22]
(b) Nguyen, T. V.; Hartmann, J. M.; Enders, D. Synthesis 2013, 45, 845.
[23]
Zhu, H. T.; Liang, C. M.; Li, T. Y.; Li, L. Y.; Zhang, R. L.; Wang, J. N.; Qi, R. Q.; Zhang, J. M.; Yang, R. H.; Yang, Y. Q.; Zhou, A. X.; Jin, X. J.; Zhou, N. N. J. Org. Chem. 2023, 88, 3409.
[24]
CCDC 2305056 (3a), 2305052 (3w), 2305058 (4a) and 2305060 (5a) contain 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.
[25]
Hajra, S.; Roy, S.; Saleh, S. A. Org. Lett. 2018, 20, 4540.
[26]
Gao, F.; Webb, J. D.; Sorek, H.; Wemmer, D. E.; Hartwig, J. F. ACS Catal. 2016, 6, 7385.
[27]
(a) Wang, H. Q.; Yang, S.; Zhang, Y. C.; Shi, F. Chin. J. Org. Chem. 2023, 43, 974 (in Chinese).
[27]
( 王海清, 杨爽, 张宇辰, 石枫, 有机化学, 2023, 43, 974.)
[27]
(b) Zhang, H. H.; Shi, F. Chin. J. Org. Chem. 2022, 42, 3351 (in Chinese).
[27]
( 张洪浩, 石枫, 有机化学, 2022, 42, 3351.)
[27]
(c) Shi, Y. C.; Yan, X. Y.; Wu, P.; Jiang, S.; Xu, R.; Tan, W.; Shi, F. Chin. J. Chem. 2023, 41, 27.
[27]
(d) Sheng, F. T.; Yang, S.; Wu, S. F.; Zhang, Y. C.; Shi, F. Chin. J. Chem. 2022, 40, 2151.
[28]
(a) Zhou, N. N.; Ning, S. S.; Tong, X. J.; Luo, T. T.; Yang, J.; Li, L. Q.; Fan, M. J.; Yang, D. S.; Zhu, H. T. J. Org. Chem. 2019, 84, 8497.
[28]
(b) Satpathi, B.; Ramasastry, S. S. V. Angew. Chem., Int. Ed. 2016, 55, 1777.
Options
Outlines

/

〈 〉