Chinese Journal of Organic Chemistry >
Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds
Received date: 2023-06-30
Revised date: 2023-09-17
Online published: 2023-09-21
In the past two decades, organosilicon compounds bearing silicon-stereogenic centers have attracted extensive attention in the fields of organic synthesis, materials, and drug design. However, the expansion of organosilicon compounds in these fields has been greatly restricted by limited source of organosilicon compounds. Therefore, the development of highly efficient and selective asymmetric catalytic methods to obtain chiral organosilicon compounds with silicon-stereogenic centers is a challenging task that needs to be solved urgently. The latest research progress on new catalytic reaction systems for asymmetric synthesis of silicon-stereogenic center containing organosilanes since 2011 is mainly summarized.
Yan Zeng , Fei Ye . Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds[J]. Chinese Journal of Organic Chemistry, 2023 , 43(10) : 3388 -3413 . DOI: 10.6023/cjoc202306027
| [1] | (a) Tacke R.; Kornek T.; Heinrich T.; Burschka C.; Penka M.; Pglm M.; Keim C.; Mutschler E.; Lambrecht G. J. Organomet. Chem. 2001, 640, 140. |
| [1] | (b) Franz A. K.; Wilson S. O. J. Med. Chem. 2013, 56, 388. |
| [1] | (c) Hirai M.; Tanaka N.; Sakai M.; Yamaguchi S. Chem. Rev. 2019, 119, 8291. |
| [1] | (d) Kan S. B. J.; Lewis R. D.; Chen K.; Arnold F. H. Science 2016, 354, 1048. |
| [1] | (e) Elbing M.; Bazan G. C. Angew. Chem., Int. Ed. 2008, 47, 834. |
| [2] | (a) Xu L. W.; Li L.; Lai G. Q.; Jiang J. X. Chem. Soc. Rev. 2011, 40, 1777. |
| [2] | (b) Shintani R. Asian J. Org. Chem. 2015, 4, 510. |
| [2] | (c) Zhang M.; Gao S.; Tang J.; Chen. L.; Liu A.; Sheng S.; Zhang A.-Q. Chem. Commun. 2021, 57, 8250. |
| [2] | (d) Wu. Y.; Wang, P. Angew. Chem., Int. Ed. 2022, 61, e202205382. |
| [2] | (e) Gao J.; He C. Chem.-Eur. J. 2022, 29, e202203475. |
| [3] | (a) Oestreich M.; Schmid U. K.; Auer G.; Keller M. Synthesis 2003, 2725. |
| [3] | (b) Rendler S.; Auer G.; Keller M.; Oestreich M. Adv. Synth. Catal. 2006, 348, 1171. |
| [3] | (c) Trzoss M.; Shao J.; Bienz S. Tetrahedron: Asymmetry 2004, 15, 1501. |
| [4] | Bai X.-F.; Zou J.-F.; Chen M.-Y.; Xu Z.; Li L.; Cui Y.-M.; Zheng Z.-J.; Xu L.-W. Chem. Asian J. 2017, 12, 1730. |
| [5] | Corriu R. J. P.; Moreau J. J. E. J. Organomet. Chem. 1976, 120, 337. |
| [6] | Xu J.-X.; Chen M.-Y. Zheng Z.-J.; Cao J.; Xu Z.; Cui Y.-M.; Xu L.-W. ChemCatChem 2017, 9, 3111. |
| [7] | Long P.-W.; Bai X.-F. Ye F.; Li L.; Xu Z.; Yang K.-F.; Cui Y.-M.; Zheng Z.-J.; Xu L.-W. Adv. Synth. Catal. 2018, 360, 2825. |
| [8] | Zhu J.; Chen S.; He C. J. Am. Chem. Soc. 2021, 143, 5301. |
| [9] | Yuan W.; Zhu X.; Xu Y.; He C. Angew. Chem., Int. Ed. 2022, 61, e202204912. |
| [10] | Yang W.; Liu L.; Guo J.; Wang S.-G.; Zhang J.-Y.; Fan L.-W.; Tian Y.; Wang L.-L.; Luan C.; Li Z.-L.; He C.; Wang X.; Gu Q.-S.; Liu X.-Y. Angew. Chem., Int. Ed. 2022, 61, e202205743. |
| [11] | Liu M.-M.; Xu Y.; He C. J. Am. Chem. Soc. 2023, 145, 11727. |
| [12] | Huang X.; Zhu J.; He C. Chin. Chem. Lett. 2023, DOI: 10.1016/j.cclet.2023.108783. |
| [13] | Tamao K.; Nakamura K.; Ishii H.; Yamaguchi S.; Shiro M. J. Am. Chem. Soc. 1996, 118, 12469. |
| [14] | Naganawa Y.; Namba T.; Kawagishi M.; Nishiyama H. Chem. Eur. J. 2015, 21, 9319. |
| [15] | Chang X.; Ma P.-L.; Chen H.-C.; Li C.-Y.; Wang P. Angew. Chem., Int. Ed. 2020, 59, 8937. |
| [16] | Huang Y.-H.; Wu Y.; Zhu Z.; Zheng S.; Ye Z.; Peng Q.; Wang P. Angew. Chem., Int. Ed. 2022, 61, e202113052. |
| [17] | Zhan G.; Teng H.-L.; Luo Y.; Nishiura M. Hou Z. Angew. Chem., Int. Ed. 2018, 130, 12522. |
| [18] | He T.; Liu L.-C.; Ma W.-P.; Li B.; Zhang Q.-W.; He W. Chem.- Eur. J. 2020, 26, 17011. |
| [19] | Wang L.; Lu W.; Zhang J.; Chong Q.; Meng F. Angew. Chem., Int. Ed. 2022, 61, e202205624 |
| [20] | Zhao Z.-Y.; Nie Y.-X.; Tang R.-H.; Yin G.-W. Cao J.; Xu Z.; Cui Y.-M.; Zheng Z.-J.; Xu L.-W. ACS Catal. 2019, 9, 9110. |
| [21] | Igawa K.; Yoshihiro D.; Ichikawa N.; Kolan N.; Tamooka K. Angew. Chem., Int. Ed. 2012, 51, 12745. |
| [22] | Wen H.; Wan X.; Huang Z. Angew. Chem., Int. Ed. 2018, 57, 6319. |
| [23] | Xie J.-L.; Xu Z.; Zhou H.-Q.; Nie Y.-X.; Cao J.; Yin G.-W.; Bouillon J.-P.; Xu L.-W. Sci. China Chem. 2021, 64, 761. |
| [24] | Ling F.-Y.; Ye F.; Fang X.-J.; Zhou X.-H.; Huang W.-S.; Xu Z.; Xu L.-W. Chem. Sci. 2023, 14, 1123. |
| [25] | Lu W.; Zhao Y.; Meng F. J. Am. Chem. Soc. 2022, 144, 5233. |
| [26] | Jin C.; He X.; Chen S.; Guo Z.; Lan Y.; Shen X. Chem 2023, 9, DOI: 10.1016/j.chempr.2023.06.014. |
| [27] | Tang R.-H.; Xu Z.; Nie Y.-X.; Xiao X.-Q.; Yang K.-F.; Xie J.-L.; Guo B.; Yin G.-W.; Yang X.-M.; Xu L.-W. iScience 2020, 23, 101268. |
| [28] | Zeng Y.; Fang X.-J.; Tang R.-H.; Xie J.-Y.; Zhang F.-J.; Xu Z.; Nie Y.-X.; Xu L.-W. Angew. Chem., Int. Ed. 2022, 61, e202214147. |
| [29] | (a) Landais Y.; Parra-Rapado L.; Planchenault D.; Weber V. Tetrahedron Lett. 1997, 38, 229. |
| [29] | (b) Gu H.; Han Z.; Xie H.; Lin X. Org. Lett. 2018, 20, 6544. |
| [29] | (c) Yang L.-L.; Ouyang J.; Zou H.-N. Zhu S.-F. Zhou Q.-L. J. Am. Chem. Soc. 2021, 143, 6401. |
| [30] | Yasutomi Y.; Suematsu H.; Katsuki T. J. Am. Chem. Soc. 2010, 132, 4510. |
| [31] | Nakagawa Y.; Chanthamath S.; Fujisawa I.; Shibatomi K.; Iwasa S. Chem. Commun. 2017, 53, 3753. |
| [32] | Jagannathan J. R.; Fettinger J. C.; Shaw J. T.; Franz A. K. J. Am. Chem. Soc. 2020, 142, 11674. |
| [33] | Kuninobu Y.; Yamauchi K.; Tamura N.; Seiki T.; Takai K. Angew. Chem., Int. Ed. 2013, 52, 1520. |
| [34] | Murai M.; Takeuchi Y.; Yamauchi K.; Kuninobu Y.; Takai K. Chem.-Eur. J. 2016, 22, 6048. |
| [35] | Murai M.; Takeshima H.; Morita H.; Kuninobu Y.; Takai K. J. Org. Chem. 2015, 80, 5407. |
| [36] | Zhang Q.-W.; An K.; Liu L.-C.; Zhang Q.; Guo H.; He W. Angew. Chem., Int. Ed. 2017, 56, 1125. |
| [37] | Mu D.; Yuan W.; Chen S.; Wang N.; Yang B.; You L.; Zu B.; Yu P.; He C. J. Am. Chem. Soc. 2020, 142, 13459. |
| [38] | Ma W.; Liu L.-C.; An K.; He T.; He W. Angew. Chem., Int. Ed. 2021, 60, 4245. |
| [39] | Chen S.; Mu D.; Mai P.-L.; Ke J.; Li Y.; He C. Nat. Commun. 2021, 12,1249. |
| [40] | Yuan W.; You L.; Lin W.; Ke J.; Li Y.; He C. Org. Lett. 2021, 23, 1367. |
| [41] | Yang B.; Yang W.; Guo Y.; You L.; He C. Angew. Chem., Int. Ed. 2020, 59, 22217. |
| [42] | Guo Y.; Liu M.-M.; Zhu X.; Zhu L.; He C. Angew. Chem., Int. Ed. 2021, 60, 13887. |
| [43] | Zhang H.; Zhao D. ACS Catal. 2021, 11, 10748. |
| [44] | Chen S.; Zhu J.; Ke J.; Li Y.; He C. Angew. Chem., Int. Ed. 2022, 61, e202117820. |
| [45] | Mu D.; Pan S.; Wang X.; Liao X.; Huang Y.; Chen J. Chem. Commun. 2022, 58, 7388. |
| [46] | Kurihara Y.; Nishikawa M.; Yamanoi Y.; Nishihara H. Chem. Commun. 2012, 48, 11564. |
| [47] | Chen L.; Huang J.-B.; Xu Z.; Zheng Z.-J.; Yang K.-F.; Cui Y.-M.; Cao J.; Xu L.-W. RSC Adv. 2016, 6, 67113. |
| [48] | Yang J.-J.; Xu Z.; Nie Y.-X.; Lu S.-Q.; Zhang J.; Xu L.-W. J. Org. Chem. 2020, 85, 14360. |
| [49] | Zhou X.-H.; Fang X.-J.; Ling. F.-Y.; Xu Z.; Hong L.-Q.; Ye F.; Xu L.-W. Org. Chem. Front. 2022, 9, 5891. |
| [50] | Shintani R.; Moriya K.; Hayashi T. ; J. Am. Chem. Soc. 2011, 133, 16440. |
| [51] | Shintani R.; Moriya K.; Hayashi T. Org. Lett. 2012, 14, 2902. |
| [52] | Chen H.; Chen Y.; Tang X.; Liu S.; Wang R.; Hu T.; Gao L.; Song Z. Angew. Chem., Int. Ed. 2019, 58, 4695. |
| [53] | Liu S.; Zhang T.; Zhu L.; Liu F.; Bai R.; Lan Y. Org. Lett. 2020, 22, 2124. |
| [54] | Luo G.; Chen L.; Li Y.; Fan Y.; Wang D.; Yang Y.; Gao L.; Jiang R.; Song Z. Org. Chem. Front. 2021, 8, 5941. |
| [55] | Chen H.; Peng J.; Pang Q.; Du H.; Huang L.; Gao L.; Lan Y.; Yang C.; Song Z. Angew. Chem., Int. Ed. 2022, 61, e202212889. |
| [56] | Chen H.; Zhang H. ; Du H.; Kuang Y.; Pang Q.; Gao L.; Wang W.; Yang C.; Song Z. Org. Lett. 2023, 25, 1558. |
| [57] | Tang X.; Zhang Y.; Tang Y.; Li Y.; Zhou J.; Wang D.; Gao L.; Su Z.; Song Z. ACS Catal. 2022, 12, 5185. |
| [58] | Wang X.; Huang S.-S.; Zhang F.-J.; Xie J.-L.; Li Z.; Xu Z.; Xu L.-W. Org. Chem. Front. 2021, 8, 6577. |
| [59] | Zhang J.; Yan N.; Ju C.-W.; Zhao D. Angew. Chem., Int. Ed. 2021, 60, 25723. |
| [60] | Wang X.-C.; Li B.; Ju C.-W.; Zhao D. Nat. Commun. 2022, 13, 3392. |
| [61] | An K.; Ma W.; Liu L.-C.; He T.; Guan G.; Zhang Q.-W.; He W. Nat. Commun. 2022, 13, 847. |
| [62] | Shintani R.; Maciver E. E.; Tamakuni F.; Hayashi T. J. Am. Chem. Soc. 2012, 134, 16955. |
| [63] | Onoe M.; Baba K.; Kim Y.; Kita Y.; Tobisu M.; Chatani N. J. Am. Chem. Soc. 2012, 134, 19477. |
| [64] | Kumar R.; Hoshimoto Y.; Yabuki H.; Ohashi M.; Ogoshi S. J. Am. Chem. Soc. 2015, 137, 11838. |
| [65] | Shintani R.; Kurata H.; Nozaki K. Chem. Commun. 2015, 51, 11378. |
| [66] | Bi X.; Feng J.; Xue X.; Gu Z. Org. Lett. 2021, 23, 3201. |
| [67] | Shintani R.; Otomo H.; Ota K.; Hayashi T. J. Am. Chem. Soc. 2012, 134, 7305. |
| [68] | Sato Y.; Takagi C.; Shintani R.; Nozaki K. Angew. Chem., Int. Ed. 2017, 56, 9211. |
| [69] | Lin Y.; Ma W.-Y.; Xu Z.; Zheng Z.-J.; Cao J.; Yang K.-F.; Cui Y.-M.; Xu L.-W. Chem. Asian J. 2019, 14, 2082. |
| [70] | Shintani R.; Takagi C.; Ito T.; Naito M.; Nozaki K. Angew. Chem., Int. Ed. 2015, 54, 1616. |
| [71] | Shintani R.; Takano R.; Nozaki K. Chem. Sci. 2016, 7, 1205. |
| [72] | Shintani R.; Misawa N.; Takano R.; Nozaki K. Chem. Eur. J. 2017, 23, 2660. |
| [73] | Long P.-W.; Xie J.-L.; Yang J.-J.; Lu S.-Q.; Xu Z.; Ye F.; Xu L.-W. Chem. Commun. 2020, 56, 4188. |
| [74] | Wang Q.; Ye F.; Cao J.; Xu Z.; Zheng Z.-J.; Xu L.-W. Catal. Commun. 2020, 138, 105950. |
| [75] | Gao J.; Mai P.-L.; Ge Y.; Yuan W.; Li Y.; He C. ACS Catal. 2022, 12, 8476. |
| [76] | Zhang G.; Li Y.; Wang Y.; Zhang Q.; Tao X.; Zhang Q. Angew. Chem., Int. Ed. 2020, 59, 11927. |
| [77] | Yin K.-L.; Zhao S.; Qin Y.; Chen S.-H.; Li B.; Zhao D. ACS Catal. 2022, 12, 13999. |
| [78] | Li S.-S.; Sun S.; Wang J. Angew. Chem., Int. Ed. 2022, 61, e202115098. |
| [79] | Qi L.; Pan Q.-Q.; Wei X.-X.; Pang X.; Liu Z.; Shu X.-Z. J. Am. Chem. Soc. 2023, 145, 13008. |
| [80] | Murata R.; Matsumoto A.; Asano K.; Matsubara S. Chem. Commun. 2020, 56, 12335. |
| [81] | Zhou H.; Han J. T.; N?thling N.; Lindner M. M.; Jennicher J.; Ku?hn C.; Tsuji N.; Zhang L.; List B. J. Am. Chem. Soc. 2022, 144, 10156. |
| [82] | Zhou H.; Properzi R.; Leutzsch M.; Belanzoni P.; Bistoni G.; Tsuji N.; Zhang L.; Han J. T.; Zhun C. List B. J. Am. Chem. Soc. 2023, 145, 4994. |
| [83] | Zhou M.; Liu J.; Deng R.; Wang Q.; Wu S.; Zheng P. ACS Catal. 2022, 12, 7781. |
| [84] | Liu H.; Zhou H.-W.; Chen X.-K.; Xu J.-F. J. Org. Chem. 2022, 87, 16127. |
| [85] | Liu H.; He P.-Y.; Liao X.-L.; Zhou Y.-P.; Chen X.-K.; Ou W.-P.; Wu Z.-H.; Luo C.; Yang L.-M.; Xu J.-F. ACS Catal. 2022, 12, 9864. |
| [86] | Liao X.-L.; Zhou H.-W.; Chen X.-K.; Xu J.-F. Org. Lett. 2023, 25, 3099. |
| [87] | Zhang D.-K; Shao Y.-B.; Xie W.-S.; Chen Y.-R.; Liu W.; Bao H.-Y.; He F.-Q.; Xue X.-S.; Yang X.-Y. ACS Catal. 2022, 12, 14609. |
| [88] | Zhang X.-X.; Gao Y.; Zhang Y.-X.; Zhou J.; Yu J.-S. Angew. Chem., Int. Ed. 2023, 62, e202217724. |
| [89] | Zhu M.; Oestreich M. ACS Catal. 2023, 13, 10244. |
| [90] | Guo W.; Li Q.; Liu Y.; Li C. Sci. China Chem. 2023, DOI: 10.1007/s11426-023-1643-7. |
/
| 〈 |
|
〉 |