Chinese Journal of Organic Chemistry >
Asymmetric Boration of para-Quinone Methides Catalyzed by N-Heterocyclic Carbene
Received date: 2021-11-30
Revised date: 2022-01-13
Online published: 2022-01-27
Supported by
National Natural Science Foundation of Shandong Province(ZR2019MB044)
The first carbene-catalyzed enantioselective 1,6-conjugate addition of boron to para-quinone methides was achieved by using the commercially available chiral triazolium and bis(pinacolato)diboron. The main features of this reaction include mild conditions, broad scope of substrates, excellent functional group tolerance, as well as good yield and enantioselectivity. Notably, in the absence of any transition metals, the reaction proceeded very well even with 0.1 mol% of catalyst loading without obvious erosion of yield and enantioselectivity, albeit longer reaction time was required.
Yuzhu Wu , Panpan Shen , Wenzeng Duan , Yudao Ma . Asymmetric Boration of para-Quinone Methides Catalyzed by N-Heterocyclic Carbene[J]. Chinese Journal of Organic Chemistry, 2022 , 42(5) : 1483 -1492 . DOI: 10.6023/cjoc202111041
| [1] | Byun, Y.; Yan, J. A.; Al-Madhoun, A. S.; Johnsamuel, J.; Yang, W.; Barth, R. F.; Eriksson, S.; Tjarks, W. J. Med. Chem. 2005, 48, 1188. |
| [2] | (a) Ohishi, T.; Nishiura, M.; and Hou, Z. Angew. Chem., Int. Ed. 2008, 47, 5792. |
| [2] | (b) Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024. |
| [2] | (c) Ding, J.; Lee, J. C. H.; Hall, D. G. Org. Lett. 2012, 14, 4462. |
| [2] | (d) Aparece, M. D.; Gao, C.; Lovinger, G. J.; Morken, J. P. Angew. Chem.,Int. Ed. 2019, 58, 592. |
| [3] | (a) Matteson, D. S. J. Org. Chem. 2013, 78, 10009. |
| [3] | (b) Sandford, C.; Aggarwal, V. K. Chem. Commun. 2017, 53, 5481. |
| [4] | (a) Das, B. C.; Thapa, P.; Karki, R.; Schinke, C.; Das, S.; Kambhampat, S.; Banerjee, S. K.; Veldhuizen, P. V.; Verma, A.; Weiss, L. M.; Evans, T. Future Med. Chem. 2013, 5, 653. |
| [4] | (b) Diaz, D. B.; Yudin, A. K. Nat. Chem. 2017, 9, 731. |
| [4] | (c) Mereddy, G. R.; Chakradhar, A.; Rutkoski, R. M.; Jonnalagadda, S. C. J. Organomet. Chem. 2018, 865, 12. |
| [5] | (a) Park, J. K.; Lackey, H. H.; Rexford, M. D.; Kovnir, K.; Shatruk, M.; McQuade, D. T. Org. Lett. 2010, 12, 5008. |
| [5] | (b) Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894. |
| [5] | (c) Hornillos, V.; Vila, C.; Otten, E.; Feringa, B. L. Angew. Chem.,Int. Ed. 2015, 54, 7867. |
| [5] | (d) Jiang, L.; Cao, P.; Wang, M.; Chen, B.; Wang, B.; Liao, J. Angew. Chem., nt. Ed. 2016, 55, 13854. |
| [5] | (e) Kubota, K.; Hayama, K.; Iwamoto, H.; Ito, H. Angew. Chem.,Int. Ed. 2015, 54, 8809. |
| [6] | (a) Carroll, A. M.; O'Sullivan, T. P.; Guiry, P. J. Adv. Synth. Catal. 2005, 347, 609. |
| [6] | (b) Zhang, L.; Zuo, Z.-Q.; Wan, X.-L.; Huang, Z. J. Am. Chem. Soc. 2014, 136, 15501. |
| [6] | (c) Dai, W.-P.; Lin, Y.-Y.; Wan, Y.; Cao, S. Org. Chem. Front. 2018, 5, 55. |
| [6] | (d) Bai, X.-Y.; Zhao, W.; Sun, X.; Li, B.-J. J. Am. Chem. Soc. 2019, 141, 19870. |
| [6] | (e) Dong, W. K.; Xu, X.; Ma, H. H.; Lei, Y. Q.; Lin, Z. Y.; Zhao, W. X. J. Am. Chem. Soc. 2021, 143, 10902. |
| [7] | Shiomi, T.; Adachi, T.; Toribatake, K.; Zhou, L.; Nishiyama, H. Chem. Commun. 2009, 5987. |
| [8] | (a) Schuster, C. H.; Li, B.; Morken, J. P. Angew. Chem., nt. Ed. 2011, 50, 7906. |
| [8] | (b) Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134. |
| [9] | (a) Mun, S.; Lee, J.-E.; Yun, J. Org. Lett. 2006, 8, 4887. |
| [9] | (b) Lee, J.-E.; Kwon, J.; Yun, J. Chem. Commun. 2008, 733. |
| [9] | (c) Lee, J.-E.; Yun, J. Angew. Chem., Int. Ed. 2008, 47, 145. |
| [9] | (d) Lillo, V.; Prieto, A.; Bonet, A.; Diaz-Requejo, M. M.; Ramirez, J.; Perez, P. J.; Fernández, E. Organometallics 2009, 28, 659. |
| [9] | (e) Meng, F. K.; McGrath, K. P.; Hoveyda, A. H. Nature 2014, 513, 367. |
| [9] | (f) Meng, F. K.; Li, X.; Torker, S.; Shi, Y.; Hoveyda, A. H. Nature 2016, 537, 387. |
| [9] | (g) Ding, W.; Song, Q. L. Org. Chem. Front. 2016, 3, 14. |
| [9] | (h) Liu, X.-X.; Zhang, W. B. Chin. J. Org. Chem. 2016, 36, 2249. (in Chinese) |
| [9] | (刘媛媛, 张万斌, 有机化学, 2016, 36, 2249.) |
| [10] | Lillo, V.; Geier, M. J.; Westcott, S. A.; Fernández, E. Org. Biomol. Chem. 2009, 7, 4674. |
| [11] | Wu, H.; Radomkit, S.; O'Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 8277. |
| [12] | (a) Wang, L.; Chen, Z.; Ma, M. M.; Duan, W. Z.; Song, C.; Ma, Y. D. Org. Biomol. Chem. 2015, 13, 10691. |
| [12] | (b) Ye, M.; Shen, P. P.; Duan, W. Z. Song, C.; Ma, Y. D. Chin. J. Org. Chem. 2017, 37, 2919. (in Chinese) |
| [12] | (叶梦, 申盼盼, 段文增, 宋淳, 马玉道, 有机化学, 2017, 37, 2919.) |
| [13] | (a) Messiano, G. B.; da Silva, T.; Nascimento, I. R.; Lopes, L. M. X. Phytochemistry 2009, 70, 590. |
| [13] | (b) Dehn, R.; Katsuyama, Y.; Weber, A.; Gerth, K.; Jansen, R.; Steinmetz, H.; Höfle, G.; Mu?ller, R.; Kirschning, A. Angew. Chem., Int. Ed. 2011, 50, 3882. |
| [13] | (c) Hamels, D.; Dansette, P. M.; Hillard, E. A.; Top, S.; Vessières, A.; Herson, P.; Jaouen, G.; Mansuy, D. Angew. Chem., Int. Ed. 2009, 48, 9124. |
| [13] | (d) Parra, A.; Tortosa, M. ChemCatChem 2015, 7, 1524. |
| [13] | (e) Wang, J.-Y.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Org. Chem. Front. 2020, 7, 1743. |
| [13] | (f) Lima, C. G. S.; Pauli, F. P.; Costa, D. C. S.; de Souza, A. S.; Forezi, L. S. M.; Ferreira, V. F.; de Carvalho da Silva, F. Eur. J. Org. Chem. 2020, 2020, 2650. |
| [14] | Lou, Y.; Cao, P.; Jia, T.; Zhang, Y.; Wang, M.; Liao, J. Angew. Chem., Int. Ed. 2015, 54, 12134. |
| [15] | Jarava-Barrera, C.; Parra, A.; López, A.; Cruz-Acosta, F.; Collado-Sanz, D.; Cárdenas, D. J.; Tortosa, M. ACS Catal. 2016, 6, 442. |
| [16] | Wu, H.; Garcia, J. M.; Haeffner, F.; Radomkit, S.; Zhugralin, A. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2015, 137, 10585. |
/
| 〈 |
|
〉 |
