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Rhodium/(2S,2'S,3S,3'S)-3,3'-Di-tert-butyl-4,4'-dimethoxy-2,2',3,3'-tetrahydro-2,2'-bibenzo[d][1,3]oxaphosphole (MeO-BIBOP) Catalyzed Synthesis of (R)-3-tert-Butoxy-carbonylamino-4-(2,4,5-trifluorophenyl)butyric Acid by Asymmetric Reduction of Enamines
Received date: 2020-11-16
Revised date: 2020-12-24
Online published: 2021-02-22
(R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid is an important pharmaceutical intermediate, so it is of great practical value to develop its highly stereoselective synthetic method. It is found that [Rh(NBD)2]+ $\mathrm{BF}_{4}^{-}$/(2S,2'S,3S,3'S)- 3,3'-di-tert-butyl-4,4'-dimethoxy-2,2',3,3'-tetrahydro-2,2'-bibenzo[d][1,3]oxaphosphole (MeO-BIBOP) catalyst has high stereoselectivity for the hydrogenation ofN-acetylenamine ester, reaching 99% ee. 2,4,5-Trifluorophenylacetic acid (1) was used as starting material, with Mildrum?s acid (2) through condensation, alcoholysis, condensation, amino acetylation, asymmetric hydrogenation, hydrolysis and amino protection to synthesize target product with 61% yield in total and 99.62% purity. It provides a practical and efficient synthetic method for its scale-up production.
Li Sheng , Haoling Gao , Xufeng Wu , Gang Fan , Pengcheng Liu . Rhodium/(2S,2'S,3S,3'S)-3,3'-Di-tert-butyl-4,4'-dimethoxy-2,2',3,3'-tetrahydro-2,2'-bibenzo[d][1,3]oxaphosphole (MeO-BIBOP) Catalyzed Synthesis of (R)-3-tert-Butoxy-carbonylamino-4-(2,4,5-trifluorophenyl)butyric Acid by Asymmetric Reduction of Enamines[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 2105 -2111 . DOI: 10.6023/cjoc202011021
| [1] | Williams, R.; Colagiuri, S.; Chan, J.; Gregg, E.; Ke, C.; Lim, L.-L.; Yang, X.-L. IDF Atlas 9th edition 2019, Brussel, 2019. |
| [2] | Li, H.; Long, Y.-Q. Chin. J. Org. Chem. 2016, 36, 736. (in Chinese). |
| [2] | (李鹤, 龙亚秋, 有机化学, 2016, 36, 736.) |
| [3] | (a) Wani, J. H.; John-Kalarickal, J.; Fonseca, V. A. Cardiol. Clin. 2008, 26, 639. |
| [3] | (b) Scheen, A. J. Acta Clin. Belg. 2008, 63, 402. |
| [4] | Anh, N. P.; Soon, W. J.; Khalilur, R. M.; Ju, B. E.; Kyung, C. M. Biochem. Pharmacol. 2019, 168, 452. |
| [5] | Yuan, K.-H.; Ma, S.-Q.; Zhu, L.; Liu, W.-H. CN 101899048, 2013. |
| [6] | Kim, D.; Wang, L.-P.; Beconi, M.; Eiermann, G. J.; Fisher, M. H.; He, H.-B.; Hickey, G. J.; Kowalchick, J. E.; Leiting, B.; Lyons, K.; Marsilio, F.; McCann, M. E.; Patel, R. A.; Petrov, A.; Scapin, G.; Patel, S. B.; Roy, R. S.; Wu, J. K.; Wyvratt, M. J.; Zhang, B. B.; Zhu, L.; Thornberry, N. A.; Weber, A. E. J. Med. Chem. 2005, 48, 141. |
| [7] | Yong, X.-L.; Hu, T.-T.; Li, N.; Feng, S.-Y.; Wang, L.-T.; Huang, J. Chin. J. New Drugs 2015, 24, 540. (in Chinese). |
| [7] | (雍小兰, 胡婷婷, 李楠, 冯仕银, 王蓝天, 黄娟, 中国新药杂志, 2015, 24, 540.) |
| [8] | Yu, Q.; Wang, T. CN 103351391, 2015. |
| [9] | (a) Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.-K.; Armstrong, J. D.; Grabowski, E. J. J.; Tillyer, R. D.; Spindler, F.; Malan, C. J. Am. Chem. Soc. 2004, 126, 9918. |
| [9] | (b) Kubryk, M.; Hansen, K. B. Tetrahedron: Asymmetry 2006, 17, 205. |
| [9] | (c) Perlman, N.; Etinger, M.; Valerie, N. H.; Abramov, M. WO 2009064476, 2009. |
| [9] | (d) Hansen, K. B.; Hsiao, Y.; Xu, F.; Rivera, N.; Clausen, A.; Kubryk, M.; Krska, S.; Rosner, T.; Simmons, B.; Balsells, J.; Ikemoto, N.; Sun, Y. K.; Spindler, F.; Malan, C.; Grabowski, E. J. J.; Armstrong, J. D. J. Am. Chem. Soc. 2009, 131, 8798. |
| [9] | (e) Wu, S.-L; Yu, B.; Wang, Y.-J.; Alain, D.; Zhu, J.-Y. US 8278486, 2012. |
| [9] | (f) Hong, J.; Wang, Y.-S.; Wang, B.-Y.; Huang, L.-N.; Gu, E. US 20170305822, 2017. |
| [9] | (g) Sreenivasulu, K.; Chaudhari, P. S.; Achanta, S.; Abhishek S.; Dahanukar, V.; Cobley, C. J.; Fiona L. B.; Bandichhor, R. Chem.- Asian J. 2020, 15, 1605. |
| [10] | (a) Ye, J.-H.; Wang, C.; Chen, L.; Wu, X.-J.; Zhou, L.; Sun, J. Adv. Synth. Catal. 2016, 358, 1042. |
| [10] | (b) Bae, H. Y.; Kim, M. J.; Sim, J. H.; Song, C. E. Angew. Chem., Int. Ed. 2016, 55, 10825. |
| [10] | (c) Jiang, H.-T.; Gao, H.-L.; Ge, C.-S. Chin. Chem. Lett. 2017, 28, 471. |
| [10] | (d) Gao, H.-L.; Yu, J.-G.; Ge, C.-S.; Jiang, Q. Molecules 2018, 23, 1440. |
| [10] | (e) Hayama, N.; Kuramoto, R.; Foldes, T.; Nishibayashi, K.; Kobayashi, Y.; Papai, I.; Takemoto, Y. J. Am. Chem. Soc. 2018, 140, 12216. |
| [11] | (a) Tasnádi, G.; Forró, E.; Fül?p, F. Org. Biomol. Chem. 2010, 8, 793. |
| [11] | (b) Zhou, S.-B.; Wang, J.; Chen, X.; Ace?a, J. L.; Soloshonok, V. A.; Liu, H. Angew. Chem., Int. Ed. 2014, 53, 7883. |
| [12] | (a) Davies, S. G.; Fletcher, A. M.; Lv, L. L.; Roberts, P. M.; Thomson, J. E. Tetrahedron Lett. 2012, 53, 3052. |
| [12] | (b) Pan, X.-H.; Li, X.-J.; Lu, Q.-L.; Yu, W.-S.; Li, W.-J.; Zhang, Q.-H.; Deng, F.; Liu, F. Tetrahedron Lett. 2013, 54, 6807. |
| [12] | (c) Anjibabu, R.; Boggu, J. M. R.; Shekhar, P.; Reddy, B. V. S. ChemistrySelect 2016, 1, 5445. |
| [12] | (d) Kang, S. K.; Cho, G. H.; Leem, H. J.; Soh, B. K.; Sim, J.; Suh, Y.-G. Tetrahedron: Asymmetry 2017, 28, 34. |
| [13] | (a) Savile C. K.; Janey J. M.; Mundorff E. C.; Moore J. C.; Tam S.; Jarvis W. R.; Colbeck J. C.; Krebber A.; Fleitz F. J.; Brangd J.; Devine P. N.; Huisman G. W.; Hughes G. J. Science 2010, 329, 305. |
| [13] | (b) Hou, A.-W.; Deng, Z.-X.; Ma, H.-M.; Liu, T.-G. Tetrahedron 2016, 72, 4660. |
| [13] | (c) Kim, G. H.; Jeon, H.; Khobragade, T. P.; Patil, M. D.; Sung, S.; Yoon, S.; Won, Y.; Choi, I. S.; Yun, H. Enzyme Microb. Technol. 2019, 120, 52. |
| [14] | (a) Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sinica 2012, 70, 1427. (in Chinese). |
| [14] | (谢建华, 周其林, 化学学报, 2012, 70, 1427.) |
| [14] | (b) Xu, R.-H.; Yang, H.; Tang, W.-J. Chin. J. Org. Chem. 2020, 40, 1409. (in Chinese). |
| [14] | (许容华, 杨贺, 汤文军, 有机化学, 2020, 40, 1409.) |
| [15] | (a) Tang, W.-J.; Capacci, A. G.; White, A.; Ma, S.-L.; Rodriguez, S.; Qu, B.; Savoie, J.; Patel, N. D.; Wei, X.-D.; Haddad, N.; Grinberg, N.; Yee, N. K.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2010, 12, 1104. |
| [15] | (b) Liu, G.-D.; Liu, X.-Q.; Cai, Z.-H.; Jiao, G.-G.; Xu, G.-Q.; Tang, W.-J. Angew. Chem., Int. Ed. 2013, 52, 4235. |
| [15] | (c) Li, W.-J.; Rodriguez, S.; Duran, A.; Sun, X.-F; Tang, W.-J.; Premasiri, A.; Wang, J.; Sidhu, K.; Patel, N. D.; Savoie, J.; Qu, B.; Lee, H.; Haddad, N.; Lorenz, J. C.; Nummy, L.; Hossain, A.; Yee, N.; Lu, B.; Senanayake, C. H. Org. Process Res. Dev. 2013, 17, 1061. |
| [16] | Ikemoto, N.; Simmons, B. L.; Williams, J. M.; Xu, F.; Yang, C.-H. WO 2004083212, 2004. |
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