Chinese Journal of Organic Chemistry >
Asymmetric Synthesis of Diarylmethanols by Chiral Phosphoramide Ligands Catalysts
Received date: 2019-02-24
Revised date: 2019-03-29
Online published: 2019-05-21
In order to improve the application of chiral phosphoramide ligands in catalytic asymmetric reactions, thiophosphoramide, which was synthesized from trans-1,2-cyclohexanediamine was used as a catalyst to synthesize chiral diarylmethanol compounds through addition reaction. The catalytic activity of the ligand in the asymmetric addition reaction of the arylalkyl zincs to the aromatic aldehyde can be as high as 94% ee under the optimized reaction conditions in the presence of 30 mol% phosphoramide ligand N-((1R,2R)-2-(isopropylamino)cyclohexyl)-P,P-diphenylphosphinic amide (9c) and the corresponding chiral diarylmethanol compound was obtained with the yields of >90%. Despite the large amount of catalyst, the ligand is very convenient to recycle and reuse in this system. At the same time, the reaction mechanism was speculated, and it is believed that the quaternary transition state and the six-element transition state formed by the reaction process are beneficial to improve the enantioselectivity of the reaction.
Qingjun Guo, . Asymmetric Synthesis of Diarylmethanols by Chiral Phosphoramide Ligands Catalysts[J]. Chinese Journal of Organic Chemistry, 2019 , 39(10) : 2912 -2919 . DOI: 10.6023/cjoc201902026
| [1] | Einhorn, A. Ber. Dtsch. Chem. Ges. 1883, 16, 2208. |
| [2] | Torrens, A.; Castrillo, J.; Claparols, A.; Redondo, J . Synlett 1999, 765. |
| [3] | (a) Casy, A. F.; Drake, A. F.; Ganellin, C. R.; Mercer, A. D.; Upton, C . Chirality 1992, 4, 356. |
| [3] | (b) Müller, P.; Nury, P.; Bernardinelli, G . Eur. J. Org. Chem. 2001, 2001, 4137. |
| [4] | Hite, G.; Barouh, V.; Dall, H.; Patel, D. J. Med. Chem. 1971, 14, 834. |
| [5] | Guo, Z.; Raeissi, S.; White, R. B.; Stevens, J. C. Drug Metab. Dispos. 1997, 25, 390. |
| [6] | Li, C.; Chauret, N.; Trimble, L. A.; Nicoll-Griffith, D. A; Silva, J. M; MacDonald, D.; Perrier, H.; Yergey, J. A.; Parton, T.; Alexander, R. P.; Warrellow, G. J. Drug Metab. Dispos. 2001, 29, 232. |
| [7] | (a) James, M. N. G.; Williams, G. J. B. Can. J. Chem. 1974, 52 1872. |
| [7] | (b) Shafi'ee, A.; Hite, G. J. Med. Chem. 1969, 12, 266. |
| [8] | (a) Bolm, C.; Hildebrand, J. P.; Mu?iz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40 3284. |
| [8] | (b) Ji, J. X.; Wu, J.; Xu, L. J.; Chiu, W. Y.; Kim, H. L.; Albert, S. C. Pure Appl. Chem. 2006; 78, 267. |
| [9] | (a) Fernández-Mateos, E.; Maciá, B.; Yus, M. Tetrahedron: Asymmetry 2012, 23, 789. |
| [9] | (b) Wu, K. H.; Gau, H. M. J. Am. Chem. Soc. 2006, 128 14808. |
| [10] | (a) Da, C.-S.; Wang, J. R.; Yin, X. G.; Fan, X. Y.; Liu, Y.; Yu, S. L . Org. Lett. 2009, 11 5578. |
| [10] | (b) Fan, X. Y.; Yang, Y. X.; Zhuo, F.-F.; Yu, S. L.; Li, X.; Guo, Q. P.; Du, Z. X.; Da, C. S . Chem.-Eur. J. 2010, 16 7988. |
| [11] | Tomita, D.; Wada, R.; Kanai, M.; Shibasaki, M . J. Am. Chem. Soc. 2005, 127, 4138. |
| [12] | Chang, S. J.; Zhou, S.; Gau, H. M . RSC Adv. 2015, 5, 9368. |
| [13] | (a) Fernández-Mateos, E.; Maciá, B.; Yus, M . Eur. J. Org. Chem. 2012, 3732. |
| [13] | (b) Nakagawa, Y.; Muramatsu, Y.; Harada, T . Eur. J. Org. Chem. 2010, 6535. |
| [14] | Bolm, C.; Rudolph, J . J. Am. Chem. Soc. 2002, 124, 14850. |
| [15] | Bauer, M.; Maurer, F.; Hoffmann, S. M.; Kazmaier, U . Synlett 2008, 3203. |
| [16] | (a) Ding, M.; Zhou, F.; Liu, Y. L.; Wang, C. H.; Zhao, X. L.; Zhou, J. Chem. Sci. 2011, 2, 2035. |
| [16] | (b) Dong, J.; Du, D. M. Org. Biomol. Chem. 2012, 10, 8125. |
| [16] | (c) Yu, Y. N.; Xu, M. H . Acta Chim. Sinica 2017, 75, 655 (in Chinese). |
| [16] | ( 于月娜, 徐明华 , 化学学报, 2017, 75, 655.) |
| [17] | Huang, H.; Bian, G.; Zong, H.; Wang, Y.; Yang, S.; Yue, H.; Song, L.; Fan, H . Org. Lett. 2016, 18, 2524. |
| [18] | Shen, B.; Huang, H.; Bian, G.; Zong, H.; Song, L. Chirality 2013, 25, 561. |
| [19] | Huang, H. Y.; Zong, H.; Shen, B.; Yue, H. F.; Bian, G. L.; Song, L. Tetrahedron 2014, 70, 1289. |
| [20] | Kaik, M.; Gawroński, J . Tetrahedron: Asymmetry 2003 14 1559. |
| [21] | Huang, H. Y.; Z ong, H.; Bian, G. L.; Song, L. J. Org. Chem. 2012, 77, 10427. |
| [22] | Yang, Y. X.; Liu, Y.; Zhang, L.; Jia, Y. E.; Wang, P.; Zhuo, F. F.; An, X. T.; Da, C. S. J. Org. Chem. 2014, 79, 10696. |
| [23] | Wu, X. Y.; Liu, X. Y.; Zhao, G. Tetrahedron: Asymmetry 2005, 16, 2299. |
| [24] | Tian, C.; Gong, L.; Meggers, E. . Chem. Commun 2016, 52, 4207. |
| [25] | Barsamian, A. L.; Wu, Z. H.; Blakemore, P. R. Org. Biomol. Chem. 2015, 13, 3781. |
| [26] | Wang, Y. B.; Zong, H.; Huang, H. Y.; Song, L . Tetrahedron: Asymmetry. 2017, 28 90. |
/
| 〈 |
|
〉 |
