Recent Advances in Catalytic Asymmetric Dihalogenation of Alkenes

doi:10.6023/cjoc202605014

Abstract

Chiral dihalogen skeletons are encountered in the structure of numerous bioactive compounds with antibacterial and antitumour activities, and widely used in the field of medicine and synthetic chemistry. Based on the importance of chiral dihalides, it is one of the important topics in organic synthetic chemistry to develop accurate, efficient, and green methods to synthesize chiral dihalides. In recent years, the synthesis of chiral dihalides by catalytic asymmetric dihalogenation of olefins has attracted great attention. Three different catalytic systems on asymmetric dihalogenation of alkenes is reviewed, including chiral Lewis base catalysis, chiral Lewis acid catalysis, and chiral organic iodine catalysis. Furthermore, the difficulties, challenges, and future development of asymmetric dihalogenation of alkenes are also discussed.

Key words: catalytic, alkene, asymmetric dihalogenation

Cite this article

Li, Jing. Recent Advances in Catalytic Asymmetric Dihalogenation of Alkenes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202605014.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] For leading reviews on intramolecular asymmetric halogenations, see: (a) Chen G.; Ma, S. Angew. Chem. Int. Ed.2010, 49, 8306.
(b) Castellanos A.; Fletcher, S. P. Chem. Eur. J.2011, 17, 5766.
(c) Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Synlett 2011, 1335.
(d) Hennecke, U. Chem. Asian J. 2012, 7, 456.
(e) Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem. Int. Ed. 2012, 51, 10938.
(f) Murai, K.; Fujioka, H. Heterocycles 2013, 87, 763.
(g) Tan, C. K.; Yeung, Y.-Y. Chem. Commun. 2013, 49, 7985.
(h) Cheng, Y. A.; Yu, W. Z.; Yeung, Y.-Y. Org. Biomol. Chem. 2014, 12, 2333.
(i) Zheng, S.; Schienebeck, C. M.; Zhang, W.; Wang, H.-Y.; Tang, W. Asian J. Org. Chem. 2014, 3, 366.
(j) Sakakura, A.; Ishihara, K. Chem. Rec. 2015, 15, 728.
(k) Ashtekar, K. D.; Jaganathan, A.; Borhan, B.; Whitehead, D. C. Org. React. 2021, 105, 1.
[2] (a) Cai Y.; Liu X.; Hui Y.; Jiang J.; Wang W.; Chen W.; Lin L.; Feng, X. Angew. Chem. Int. Ed.2010, 49, 6160.
(b) Cai Y.; Liu X.; Jiang J.; Chen W.; Lin L.; Feng, X. J. Am. Chem. Soc.2011, 133, 5636.
(c) Cai, Y.; Liu, X.; Li, J.; Chen, W.; Wang, W.; Lin, L.; Feng, X. Chem. Eur. J. 2011, 17, 14916.
(d) Cai, Y.; Liu, X.; Zhou, P.; Kuang, Y.; Lin, L.; Feng, X. Chem. Commun. 2013, 49, 8054.
(e) Wang, Z.; Lin, L.; Zhou, P.; Liu, X.; Feng, X. Chem. Commun. 2017, 53, 3462.
(f) Cai, Y.; Liu, X.; Zhou, P.; Feng, X. J. Org. Chem. 2019, 84, 1.
[3] Zhou P.; Cai Y.; Zhong X.; Luo W.; Kang T.; Li J.; Liu X.; Lin L.; Feng X. ACS Catal.2016, 6, 7778.
[4] Zhou P.; Lin L.; Chen L.; Zhong X.; Liu X.; Feng, X. J. Am. Chem. Soc.2017, 139, 13414.
[5] Li W.; Zhou P.; Li G.; Lin L.; Feng X.Adv. Synth. Catal. 2020, 362, 1982.
[6] Alix A.; Lalli C.; Retailleau P.; Masson, G. J. Am. Chem. Soc.2012, 134, 10389.
[7] Honjo T.; Phipps R. J.; Rauniyar V.; Toste, F. D. Angew. Chem. Int. Ed.2012, 51, 9684.
[8] Zhang W.; Liu N.; Schienebeck C. M.; Zhou X.; Izhar I. I.; Guzei I. A.; Tang W. Chem. Sci.2013, 4, 2652.
[9] Zhang Y.; Xing H.; Xie W.; Wan X.; Lai Y.; Ma, D. Adv. Synth. Catal.2013, 355, 68.
[10] Qi J.; Fan G.-T.; Chen J.; Sun M.-H.; Dong Y.-T.; Zhou L. Chem. Commun.2014, 50, 13841.
[11] Li L.; Su C.; Liu X.; Tian H.; Shi Y. Org. Lett.2014, 16, 3728.
[12] (a) Zhang X.; Li J.; Tian H.; Shi, Y. Chem. Eur. J.2015, 21, 11658.
(b) Li, J.; Li, Z.; Zhang, X.; Xu, B.; Shi, Y. Org. Chem. Front. 2017, 4, 1084.
(c) Li, J.; Shi, Y. RSC Adv. 2021, 11, 13040.
(d) Li, J.; Wang, Z.; Wang, X.; Tetrahedron Chem 2023, 6, 100039.
[13] Soltanzadeh B.; Jaganathan A.; Staples R. J.; Borhan, B. Angew. Chem. Int. Ed.2015, 54, 9517.
[14] Cao Y.-M.; Lentz, D., Christmann, M. J. Am. Chem. Soc.2018, 140, 10677.
[15] (a) Cresswell A. J.; Eey S. T.-C.; Denmark, S. E. Angew. Chem. Int. Ed.2015, 54, 15642.
(b) He, T.; Zeng, X. Chin. J. Org. Chem. 2017, 37, 798(in Chinese).
(何天雄, 曾祥华, 有机化学, 2017, 37, 798.).
(c) Bock, J.; Guria, S.; Wedek, V.; Hennecke, U. Chem. Eur. J. 2021, 27, 4517.
(d) Dong, J.-W.; Cao, R.-F.; Chen, Z.-M. Synlett 2022, 33, 1819.
(e) Landry, M. L.; Burns, N. Z. Acc. Chem. Res. 2018, 51, 1260.
[16] (a) Butler, A.; Walker, J. V.Chem. Rev. 1993, 93, 1937.
(b) Vaillancourt F. H.; Yeh E.; Vosburg D. A.; Garneau-Tsodikova S.; Walsh, C. T. Chem. Rev.2006, 106, 3364.
(c) Frank, A.; Seel, C. J.; Groll, M.; Gulder, T. ChemBioChem 2016, 17, 2028.
(d) Fuller, R. W.; Cardellina II, J. H., Kato, Y.; Brinen, L. S.; Clardy, J.; Snader, K. M.; Boyd, M. R. J. Med. Chem. 1992, 35, 3007.
(e) Andrianasolo, E. H.; France, D.; Cornell-Kennon, S.; Gerwick, W. H. J. Nat. Prod. 2006, 69, 576.
(f) Vogel, C. V.; Pietraszkiewicz, H.; Sabry, O. M.; Gerwick, W. H.; Valeriote, F. A.; Vanderwal, C. D. Angew. Chem., Int. Ed. 2014, 53, 12205.
[17] Nicolaou K. C.; Simmons N. L.; Ying Y.; Heretsch P. M.; Chen, J. S. J. Am. Chem. Soc.2011, 133, 8134.
[18] Soltanzadeh B.; Jaganathan A.; Yi Y.; Yi H.; Staples R. J.; Borhan B.J. Am. Chem. Soc. 2017, 139, 2132.
[19] Wedek V.; Lommel R. V.; Daniliuc C. G.; Proft F. D.; Hennecke, U. Angew. Chem. Int. Ed.2019, 58, 9239.
[20] Wu S.; Xiang S.-H.; Li S.; Ding W.-Y.; Zhang L.; Jiang P.-Y.; Zhou Z.-A.; Tan B. Nat. Catal.2021, 4, 692.
[21] Chang Y.; Xu D.; Zhou G.; Liu B.; Zhou H.; Qin W.; Yan, H. J. Am. Chem. Soc.2026, 148, 547.
[22] Lubaev A. E.; Rathnayake M. D.; Eze F.; Bayeh-Romero, L. J. Am. Chem. Soc.2022, 144, 13294.
[23] Gilbert B. B.; Eey S. T.-C.; Ryabchuk P.; Garry O.; Denmark S. E. Tetrahedron2019, 75, 4086.
[24] Hu D. X.; Shibuya G. M.; Burns, N. Z. J. Am. Chem. Soc.2013, 135, 12960.
[25] Hu D. X.; Seidl F. J.; Bucher C.; Burns, N. Z. J. Am. Chem. Soc.2015, 137, 3795.
[26] Bucher C.; Deans R. M.; Burns, N. Z. J. Am. Chem. Soc.2015, 137, 12784.
[27] Huang W.-S.; Chen L.; Zheng Z.-J.; Yang K.-F.; Xu Z.; Cui Y.-M.; Xu, L.-W. Org. Biomol. Chem.2016, 14, 7927.
[28] Landry M. L.; Hu D. X.; McKenna G. M.; Burns, N. Z. J. Am. Chem. Soc.2016, 138, 5150.
[29] Zhang D.; Pu M.; Liu Z.; Zhou Y.; Yang Z.; Liu X.; Wu Y.-D.; Feng, X. J. Am. Chem. Soc.2023, 145, 4808.
[30] Banik S. M.; Medley J. W.; Jacobsen, E. N. J. Am. Chem. Soc.2016, 138, 5000.
[31] Banik S. M.; Medley J. W.; Jacobsen E. N.Science 2016, 353, 51.
[32] Zhou B.; Haj M. K.; Jacobsen E. N.; Houk K. N.; Xue X.-S.; J. Am. Chem. Soc.2018, 140, 15206.
[33] Haj M. K.; Banik S. M.; Jacobsen, E. N. Org. Lett.2019, 21, 4919.
[34] Scheidt F.; Schäfer M.; Sarie J. C.; Daniliuc C. G.; Molloy J. J.; Gilmour, R. Angew. Chem. Int. Ed.2018, 57, 16431.
[35] Sarie J. C.; Neufeld J.; Daniliuc C. G.; Gilmour R. ACS Catal.2019, 9, 7232.

烯烃的催化不对称双卤化研究进展