Chinese Journal of Organic Chemistry >
Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis
Received date: 2022-08-31
Revised date: 2022-10-20
Online published: 2022-10-25
Supported by
National Key R&D Program of China(2021YFF0701600); National Natural Science Foundation of China(22031004); National Natural Science Foundation of China(21921003); National Natural Science Foundation of China(91956128); Science and Technology Commission of Shanghai Municipality(21ZR1445900); Shanghai Municipal Education Commission(20212308)
Compounds bearing phosphorus, sulfur or silicon stereogenic center have a wide range of applications in the fields of medicine, pesticides, organic synthesis and material science. Efficient construction of these three types of heteroatom-centered chirality has gradually developed as one of the most important frontiers in asymmetric synthetic chemistry. This paper focuses on the recent development of the asymmetric synthesis via palladium/chiral complexes or using the chiral auxiliaries. Strategies such as P—X (X=H, Si or O) bond activation, desymmetrization, and cycloaddition for P-chiral compounds synthesis are introduced, while the methods for S and Si chiral compounds are somewhat similar. The mechanism of some representative examples and their potential applications are also included.
Key words: palladium catalysis; P-chirality; S-chirality; Si-chirality; asymmetric catalysis
Jieming Zhang , Hang Ni , Qi Wu , Junfeng Yang , Junliang Zhang . Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3118 -3128 . DOI: 10.6023/cjoc202208043
| [1] | (a) De Clercq, E. Clin. Microbiol. Rev. 2003, 16, 569. |
| [1] | (b) Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107, 5133. |
| [1] | (c) Akiyama, T. Chem. Rev. 2007, 107, 5744. |
| [1] | (d) Lamberth, C. Tetrahedron 2010, 66, 7239. |
| [1] | (e) Kazemi, M.; Tahmasbi, A.; Valizadeh, R.; Naserian, A.; Soni, A. Agric. Sci. Res. J. 2012, 2, 512. |
| [1] | (f) Lu, D.; Salem, G. Coord. Chem. Rev. 2013, 257, 1026. |
| [1] | (g) Yao, Q.; Wang, A.; Pu, J.; Tang, Y. Chin. J. Org. Chem. 2014, 34, 292. (in Chinese). |
| [1] | (姚秋丽, 王安俊, 蒲家志, 唐瑜敏, 有机化学, 2014, 34, 292.) |
| [1] | (h) Chen, T.; Han, L. Synlett 2015, 26, 1153. |
| [1] | (i) Khan, A.; Foucher, D. Coord. Chem. Rev. 2016, 312, 41. |
| [2] | (a) Liu, S.; Li, Y.; Wang, D.; Wei, R.; Miao, Z. Chin. J. Org. Chem. 2018, 38, 341. (in Chinese). |
| [2] | (刘双, 李玉明, 王典, 魏榕, 苗志伟, 有机化学, 2018, 38, 341.) |
| [2] | (b) Zhu, R.; Liao, K.; Yu, J.; Zhou, J. Acta Chim. Sinica 2020, 78, 193. (in Chinese). |
| [2] | (朱仁义, 廖奎, 余金生, 周剑, 化学学报, 2020, 78, 341.) |
| [3] | Mikołajczyk, M.; Drabowicz, J.; Kiełbasi´nski, P. Chiral Sulfur Reagents: Applications in Asymmetric and Stereoselective Synthesis, CRC Press, Boca Raton, USA, 1997. |
| [4] | (a) Pope, W.; Peachey, S. J. Chem. Soc. 1900, 1072. |
| [4] | (b) Wojaczyńska, E.; Wojaczyński, J. Chem. Rev. 2010, 110, 4303. |
| [4] | (c) Drabowicz, J. Phosphorus, Sulfur Silicon Relat. Elem. 2017, 192, 145. |
| [4] | (d) Han, J.; Soloshonok, V.; Klika, K.; Drabowicz, J.; Wzorek A. Chem. Soc. Rev. 2018, 47, 1307. |
| [4] | (e) Wojaczyńska, E.; Wojaczyński, J. Chem. Rev. 2020, 120, 4578. |
| [5] | (a) Sommer, L.; Frye, C. J. Am. Chem. Soc. 1959, 81, 1013. |
| [5] | (b) Sommer, L.; Frye, C.; Parker, G.; Michael, K. J. Am. Chem. Soc. 1964, 86, 3271. |
| [5] | (c) Djerourou, A.; Blaneo, L. Tetrahedron Lett. 1991, 32, 6325. |
| [5] | (d) Jankowski, P.; Schaumann, E.; Wicha, J.; Zarecki, A.; Adiwidjaja, G.; Asztemborska, M. Chem. Commun. 2000, 2030. |
| [6] | (a) Xu, L.; Li, L.; Lai, G.; Jiang, J. Chem. Soc. Rev. 2011, 40, 1777. |
| [6] | (b) Chen, C.; Hartwig, J. Chem. Rev. 2015, 115, 8946. |
| [6] | (c) Boon, L.; Fuku-en, S.; Slootweg, J.; Lammertsma, K.; Ehlers, A. Top. Catal. 2018, 61, 674. |
| [7] | (a) Cui, Y.; Lin, Y.; Xu, L. Coord. Chem. Rev. 2017, 330, 37. |
| [7] | (b) Diesel, J.; Cramer, N. ACS Catal. 2019, 9, 9164. |
| [8] | Oshiki, T.; Imamoto, T. J. Am. Chem. Soc. 1992, 114, 3975. |
| [9] | Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776. |
| [10] | (a) Moncarz, J.; Brunker, T.; Glueck, D.; Sommer, R.; Rheingold, A. J. Am. Chem. Soc. 2003, 125, 1180. |
| [10] | (b) Moncarz, J.; Brunker, T.; Jewett, J.; Orchowski, M.; Glueck, D. Organometallics 2003, 22, 3205. |
| [11] | (a) Blank, N.; Moncarz, J.; Brunker, T.; Scriban, C.; Anderson, B.; Amir, O.; Glueck, D.; Zakharov, L.; Golen, J.; Incarvito, C.; Rheingold, A. J. Am. Chem. Soc. 2007, 129, 6847. |
| [11] | (b) Huang, Y.; Li, Y.; Leung, P.; Hayashi, T. J. Am. Chem. Soc. 2014, 136, 4865. |
| [12] | Dai, Q.; Li, W.; Li, Z.; Zhang, J. J. Am. Chem. Soc. 2019, 141, 20556. |
| [13] | (a) Join, B.; Mimeau, D.; Delacroix, O.; Gaumont, A. Chem. Commun. 2006, 3249. |
| [13] | (b) Dai, Q.; Liu, L.; Qian, Y.; Li, W.; Zhang, J. Angew. Chem., Int. Ed. 2020, 59, 20645. |
| [13] | (c) Xie, X.; Li, S.; Chen, Q.; Guo, H.; Yang, J.; Zhang, J. Org. Chem. Front. 2022, 9, 1589. |
| [13] | (d) Brunker, T.; Anderson, B.; Blank, N.; Glueck, D.; Rheingold, A. Org. Lett. 2007, 9, 1109. |
| [14] | Chan, V.; Bergman, R.; Toste, F. J. Am. Chem. Soc. 2007, 129, 15122. |
| [15] | Lian, Z.; Bhawal, B.; Yu, P.; Morandi, B. Science 2017, 356, 1059. |
| [16] | (a) Anirban Mondal, A.; Thiel, N.; Dorel, R.; Feringa, B. Nat. Catal. 2022, 5, 10. |
| [16] | (b) Imrie, C.; Modro, T.; Rooyen, P.; Wagener, C.; Wallace, K.; Hudson, H.; McPartlin, M.; Nasirun, J.; Powroznyk, L. J. Phys. Org. Chem. 1995, 8, 41. |
| [17] | Deng, H.; Wang, M.; Liang, Y.; Chen, X.; Wang, T.; Wong, J.; Zhao, Y.; Houk, K.; Shi, Z. Chem 2022, 8, 569. |
| [18] | (a) Du, Z.; Guan, J.; Wu, G.; Xu, P.; Gao, L.; Han, F. J. Am. Chem. Soc. 2015, 137, 632. |
| [18] | (b) Lin, Z.; Wang, W.; Yan, S.; Duan, W. Angew. Chem., Int. Ed. 2015, 54, 6265. |
| [18] | (c) Liu, L.; Zhang, A.; Wang, Y.; Zhang, F.; Zuo, Z.; Zhao, W.; Feng, C.; Ma, W. Org. Lett. 2015, 17, 2046. |
| [18] | (d) Xu, G.; Li, M.; Wang, S.; Tang, W. Org. Chem. Front. 2015, 2, 1342. |
| [18] | (e) Lin, Y.; Ma, W.; Sun, Q.; Cui, Y.; Xu, L. Synlett 2017, 28, 1432. |
| [18] | (f) Li, Z.; Lin, Z.; Yan, C.; Duan, W. Organometallics 2019, 38, 3916. |
| [19] | (a) Kolodiazhnyi, O. Tetrahedron Asymmetry 2012, 23, 1. |
| [19] | (b) Montchamp, J. Phosphorus Chemistry I: Asymmetric Synthesis and Bioactive Compounds, Springer, Cham, 2015. |
| [20] | (a) Leung, P; He, G.; Lang, H.; Liu, A.; Loh, S; Selvaratnam, S.; Mok, K.; White, A.; Williams, D. Tetrahedron 2000, 56, 7. |
| [20] | (b) Chen, S.; Pullarkat, S.; Li, Y.; Leung, P. Eur. J. Inorg. Chem. 2011, 3111. |
| [20] | (c) He, G.; Loh, S.; Vittal, J.; Mok, K.; Leung, P. Organometallics 1998, 17, 3931. |
| [21] | Maitro, G.; Vogel, S.; Prestat, G.; Madec, D.; Poli, G. Org. Lett. 2006, 8, 5951. |
| [22] | Maitro, G.; Vogel, S.; Sadaoui, M.; Prestat, G.; Madec, D.; Poli, G. Org. Lett. 2007, 9, 5493. |
| [23] | Wang, L.; Chen, M.; Zhang, P.; Li, W.; Zhang, J. J. Am. Chem. Soc. 2018, 140, 3467. |
| [24] | Chen, W.; Berritt, S.; Liang, X.; Walsh, P. Org. Lett. 2019, 21, 960. |
| [25] | Zhu, Y.; Li, Y.; Zhang, B.; Zhang, F.; Yang, Y.; Wang, X. Angew. Chem., Int. Ed. 2018, 57, 5129. |
| [26] | Mukherjee, K.; Grimblat, N.; Sau, S.; Ghosh, K.; Shankar, M.; Gandon, V.; Sahoo, A. Chem. Sci. 2021, 12, 14863. |
| [27] | Shintani, R.; Moriya, K.; Hayashi, T. J. Am. Chem. Soc. 2011, 133, 16440. |
| [28] | (a) Shintani, R.; Moriya, K.; Hayashi, T. Org. Lett. 2012, 14, 2902. |
| [28] | (b) Xie, J.; Xu, Z.; Zhou, H.; Nie, Y.; Cao, J.; Yin, G.; Bouillon, J.; Xu, L. Sci. China: Chem. 2021, 64, 761. |
| [29] | Zhang, J.; Xu, J.; Zheng, Z.; Xu, Z.; Cui, Y.; Cao, J.; Xu, L. Chem. Asian J. 2016, 11, 2867. |
| [30] | Shintani, R.; Otomo, H.; Ota, K.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 7305. |
| [31] | Kurihara, Y.; Nishikawa, M.; Yamanoi, Y.; Nishihara, H. Chem. Commun. 2012, 48, 11564. |
| [32] | (a) Chen, L.; Huang, J.; Xu, Z.; Zheng, Z.; Yang, K.; Cui, Y.; Cao, J.; Xu, L. RSC Adv. 2016, 6, 67113. |
| [32] | (b) Yang, J.; Xu, Z.; Nie, Y.; Lu, S.; Zhang, J.; Xu, L. J. Org. Chem. 2020, 85, 14360. |
| [33] | Lin, Y.; Ma, W.; Xu, Z.; Zheng, Z.; Cao, J.; Yang, K.; Cui, Y.; Xu, L. Chem. Asian J. 2019, 14, 2082. |
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