Chinese Journal of Organic Chemistry >
Recent Advances in Catalytic Asymmetric Synthesis of Chiral 1,2-Bis(boronic) Esters
Received date: 2023-12-15
Revised date: 2024-01-13
Online published: 2024-01-30
Supported by
National Natural Science Foundation of China(22101177); Science and Technology Commission of Shanghai Municipality(21ZR1442000); Science and Technology Commission of Shanghai Municipality(23YF1426700)
Chiral 1,2-bis(boronic) esters are essential building blocks in the field of synthetic chemistry, and their catalytic asymmetric synthesis has attracted significant interest of chemists. Recently, asymmetric diboration of olefins, using transition metals and chiral diols, has emerged as the straightforward and atom-economical methods for producing highly valuable chiral 1,2-bis(boronic) esters. Asymmetric hydrogenation of vinyl bis(boronic) esters can be a complementary approach to asymmetric diboration for synthesizing these products. Additionally, borofunctionalization of alkenes or alkynes represents another effective strategy for constructing these highly valuable scaffolds. A recent innovation involves catalytic asymmetric migratory coupling reactions with gem-diborylalkanes, offering new avenues for synthesizing chiral 1,2-bis(boronic) esters. The latest developements and challenges in synthesizing these moleculeshis are summarized, and the potential future research directions in this field are prospected.
Chonglei Ji , Dewei Gao . Recent Advances in Catalytic Asymmetric Synthesis of Chiral 1,2-Bis(boronic) Esters[J]. Chinese Journal of Organic Chemistry, 2024 , 44(5) : 1385 -1402 . DOI: 10.6023/cjoc202312014
| [1] | (a) Caldwell, J. J. Clin. Pharmacol. 1992, 32, 925. |
| [1] | (b) Jozwiak, K.; Lough, W. J.; Wainer, I. W. Drug Stereochemistry: Analytical Methods and Pharmacology, 3rd ed., Informa, New York, 2012. |
| [1] | (c) Rentsch, K. M. J. Biochem. Biophys. Methods 2002, 54, 1. |
| [2] | (a) Hall, D. G. Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2nd ed., Wiley-VCH, Weinheim, Germany, 2011. |
| [2] | (b) Trippier, P. C.; McGuigan, C. Med. Chem. Commun. 2010, 1, 183. |
| [2] | (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. |
| [2] | (d) Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722. |
| [2] | (e) Xu, L.; Zhang, S.; Li, P. Chem. Soc. Rev. 2015, 44, 8848. |
| [2] | (f) Brooks, W. L. A.; Sumerlin, B. S. Chem. Rev. 2016, 116, 1375. |
| [2] | (g) Diner, C.; Szabó, K. J. J. Am. Chem. Soc. 2017, 139, 2. |
| [2] | (h) Fyfe, J. W. B.; Watson, A. J. B. Chem 2017, 3, 31. |
| [2] | (i) Rygus, J. P. G.; Crudden, C. M. J. Am. Chem. Soc. 2017, 139, 18124. |
| [2] | (j) Namirembe, S.; Morken, J. P. Chem. Soc. Rev. 2019, 48, 3464. |
| [2] | (k) He, Z.; Hu, Y.; Xia, C.; Liu, C. Org. Biomol. Chem. 2019, 17, 6099. |
| [2] | (l) Kischkewitz, M.; Friese, F. W.; Studer, A. Adv. Synth. Catal. 2020, 362, 2077. |
| [2] | (m) Kalita, S. J.; Cheng, F.; Huang, Y.-Y. Adv. Synth. Catal. 2020, 362, 2778. |
| [2] | (n) Yang, K.; Song, Q. Acc. Chem. Res. 2021, 54, 2298. |
| [2] | (o) Yeung, K.; Mykura, R. C.; Aggarwal, V. K. Nat. Synth. 2022, 1, 117. |
| [2] | (p) Jiang, X.-M.; Liu, X.-R.; Chen, A.; Zou, X.-Z.; Ge, J.-F.; Gao, D.-W. Eur. J. Org. Chem. 2022, e202101463. |
| [3] | (a) Viso, A.; Fernández de la Pradilla, R.; Tortosa, M. ACS Catal. 2022, 12, 10603. |
| [3] | (b) Wang, X.; Wang, Y.; Huang, W.; Xia, C.; Wu, L. ACS Catal. 2021, 11, 1. |
| [4] | (a) Mlynarski, S. N.; Schuster, C. H.; Morken, J. P. Nature 2014, 505, 386. |
| [4] | (b) Blaisdell, T. P.; Morken, J. P. J. Am. Chem. Soc. 2015, 137, 8712. |
| [4] | (c) Crudden, C. M.; Ziebenhaus, C.; Rygus, J. P. G.; Ghozati, K.; Unsworth, P. J.; Nambo, M.; Voth, S.; Hutchinson, M.; Laberge, V. S.; Maekawa, Y.; Imao, D. Nat. Commun. 2016, 7, 11065. |
| [4] | (d) Fawcett, A.; Nitsch, D.; Ali, M.; Bateman, J. M.; Myers, E. L.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2016, 55, 14663. |
| [4] | (e) Liu, X.; Sun, C.; Mlynarski, S.; Morken, J. P. Org. Lett. 2018, 20, 1898. |
| [4] | (f) Davenport, E.; Fernandez, E. Chem. Commun. 2018, 54, 10104. |
| [4] | (g) Fawcett, A.; Murtaza, A.; Gregson, C. H. U.; Aggarwal, V. K. J. Am. Chem. Soc. 2019, 141, 4573. |
| [4] | (h) Namirembe, S.; Yan, L.; Morken, J. P. Org. Lett. 2020, 22, 9174. |
| [4] | (i) Willems, S.; Toupalas, G.; Reisenbauer, J. C.; Morandi, B. A. Chem. Commun. 2021, 57, 3909. |
| [4] | (j) Mali, M.; Sharma, G. V. M.; Ghosh, S.; Roisnel, T.; Carboni, B.; Berrée, F. J. Org. Chem. 2022, 87, 7649. |
| [4] | (k) Xu, N.; Kong, Z.; Wang, J. Z.; Lovinger, G. J.; Morken, J. P. J. Am. Chem. Soc. 2022, 144, 17815. |
| [4] | (l) Zhang, M.; Lee, P. S.; Allais, C.; Singer, R. A.; Morken, J. P. J. Am. Chem. Soc. 2023, 145, 8308. |
| [5] | Ma, X.; Murray, B.; Biscoe, M. R. Nat. Rev. Chem. 2020, 4, 584. |
| [6] | Blair, D. J.; Tanini, D.; Bateman, J. M.; Scott, H. K.; Myers, E. L.; Aggarwal, V. K. Chem. Sci. 2017, 8, 2898. |
| [7] | (a) Coombs. J. R.; Morken. J. P. Angew. Chem., Int. Ed. 2016, 55, 2636. |
| [7] | (b) Obligacion, J. V.; Chirik, P. J. Nat. Rev. Chem. 2018, 2, 15. |
| [7] | (c) Wang, F.; Chen, P.; Liu, G. Acc. Chem. Res. 2018, 51, 2036. |
| [7] | (d) Chen, J.-H.; Guo. J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075. |
| [7] | (e) Li, Z.-L.; Fang, G.-C.; Gu, Q.-S.; Liu, X.-Y. Chem. Soc. Rev. 2020, 49, 32. |
| [8] | Morgan, J. B.; Miller, S. P.; Morken, J. P. J. Am. Chem. Soc. 2003, 125, 8702. |
| [9] | Miller, S. P.; Morgan, J. B.; Nepveux, V. F. J.; Morken, J. P. Org. Lett. 2004, 6, 131. |
| [10] | Trudeau, S.; Morgan, J. B.; Shrestha, M.; Morken, J. P. J. Org. Chem. 2005, 70, 9538. |
| [11] | Toribatake, K.; Nishiyama, H. Angew. Chem., Int. Ed. 2013, 52, 11011. |
| [12] | Pelz, N. F.; Woodward, A. R.; Burks, H. E.; Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 16328. |
| [13] | Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2006, 128, 74. |
| [14] | Woodward, A. R.; Burks, H. E.; Chan, L. M.; Morken, J. P. Org. Lett. 2005, 7, 5505. |
| [15] | Pelz, N. F.; Morken, J. P. Org. Lett. 2006, 8, 4557. |
| [16] | Kliman, L. T.; Mlynarski, S. N.; Ferris, G. E.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 13210. |
| [17] | (a) Kliman, L. T.; Mlynarski, S. N.; Morken, J. P. Angew. Chem., Int. Ed. 2012, 51, 512. |
| [17] | (b) Coombs, J. R.; Haeffner, F.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 11222. |
| [18] | Ferris, G. E.; Hong, K.; Roundtree, I. A.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 2501. |
| [19] | Coombs, J. R.; Zhang, L.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 16140. |
| [20] | (a) Byrom, N. T.; Grigg, R.; Kongkathip, B.; Reimer, G.; Wade, A. R. J. Chem. Soc., Perkin Trans. 1 1984, 1643. |
| [20] | (b) Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. Tetrahedron Lett. 1986, 27, 3535. |
| [20] | (c) Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1988, 356. |
| [20] | (d) Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1990, 1375. |
| [20] | (e) Mayer, S. F.; Mang, H.; Steinreiber, A.; Saf, R.; Faber, K. Can. J. Chem. 2002, 80, 362. |
| [21] | Nóvoa, L.; Trulli, L.; Parra, A.; Tortosa, M. Angew. Chem., Int. Ed. 2021, 60, 11763. |
| [22] | (a) Bonet, A.; Sole, C.; Gulyás, H.; Fernández, E. Org. Biomol. Chem. 2012, 10, 6621. |
| [22] | (b) Bonet, A.; Pubill-Ulldemolins, C.; Bo, C.; Gulyás, H.; Fernández, E. Angew. Chem., Int. Ed. 2011, 50, 7158. |
| [23] | Fang, L.; Yan, L.; Haeffner, F.; Morken, J. P. J. Am. Chem. Soc. 2016, 138, 2508. |
| [24] | Yan, L.; Meng, Y.; Haeffner, F.; Leon, R. M.; Crockett, M. P.; Morken, J. P. J. Am. Chem. Soc. 2018, 140, 3663. |
| [25] | Yan, L.; Morken, J. P. Org. Lett. 2019, 21, 3760. |
| [26] | Lee, Y.; Jang, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 18234. |
| [27] | Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3160. |
| [28] | Jung, H.-Y.; Yun, J. Org. Lett. 2012, 14, 2606. |
| [29] | Zanghi, J. M.; Liu, S.; Meek, S. J. Org. Lett. 2019, 21, 5172. |
| [30] | Radomkit, S.; Liu, Z.; Closs, A.; Mikus, M. S.; Hoveyda, A. H. Tetrahedron 2017, 73, 5011. |
| [31] | Lee, H.; Lee, S.; Yun, J. ACS Catal. 2020, 10, 2069. |
| [32] | Green, J. C.; Joannou, M. V.; Murray, S. A.; Zanghi, J. M.; Meek, S. J. ACS Catal. 2017, 7, 4441. |
| [33] | Fan, Z.; Ye, M.; Wang, Y.; Qiu, J.; Li, W.; Ma, X.; Yang, K.; Song, Q. ACS Cent. Sci. 2022, 8, 1134. |
| [34] | Morgan, J. B.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 15338. |
| [35] | Paptchikhine, A.; Cheruku, P.; Engman, M.; Andersson, P. G. Chem. Commun. 2009, 5996. |
| [36] | (a) Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633. |
| [36] | (b) Pye, D. R.; Mankad, N. P. Chem. Sci. 2017, 8, 1705. |
| [36] | (c) Fu, J.; Huo, X.; Li, B.; Zhang, W. Org. Biomol. Chem. 2017, 15, 9747. |
| [36] | (d) Kim, U. B.; Jung, D. J.; Jeon, H. J.; Rathwell, K.; Lee, S.-g. Chem. Rev. 2020, 120, 13382. |
| [36] | (e) Tian, F.; Zhang, J.; Yang, W.-L.; Deng, W.-P. Chin. J. Org. Chem. 2020, 40, 3262. |
| [36] | (f) Huo, X.; Li, G.; Wang, X.; Zhang, W. Angew. Chem., Int. Ed. 2022, 61, e202210086. |
| [36] | (g) Wei, L.; Wang, C.-J. Chin. J. Chem. 2021, 39, 15. |
| [36] | (h) Martínez, S.; Veth, L.; Lainer, B.; Dydio, P. ACS Catal. 2021, 11, 3891. |
| [36] | (i) Wei, L.; Wang, C.-J. Chem. Catal. 2023, 3, 100455. |
| [37] | (a) Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928. |
| [37] | (b) Wang, B.; Wu, F.; Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2007, 129, 768. |
| [37] | (c) Zhu, B.; Lee, R.; Li, J.; Ye, X.; Hong, S.-N.; Qiu, S.; Coote, M. L.; Jiang, Z. Angew. Chem., Int. Ed. 2016, 55, 1299. |
| [37] | (d) Li, Z.; Hu, B.; Wu, Y.; Fei, C.; Deng, L. Proc. Natl. Acad. Sci. U. S. A. 2018, 115, 1730. |
| [37] | (e) Trost, B. M.; Zell, D.; Hohn, C.; Mata, G.; Maruniak, A. Angew. Chem., Int. Ed. 2018, 57, 12916. |
| [37] | (f) Trost, B. M.; Schultz, J. E.; Chang, T.; Maduabum, M. R. J. Am. Chem. Soc. 2019, 141, 9521. |
| [37] | (g) Yang, S.-Q.; Wang, Y.-F.; Zhao, W.-C.; Lin, G.-Q.; He, Z.-T. J. Am. Chem. Soc. 2021, 143, 7285. |
| [37] | (h) Zhang, J.; Huo, X.; Xiao, J.; Zhao, L.; Ma, S.; Zhang, W. J. Am. Chem. Soc. 2021, 143, 12622. |
| [37] | (i) Dai, J.; Li, L.; Ye, R.; Wang, S.; Wang, Y.; Peng, F.; Shao, Z. Angew. Chem., Int. Ed. 2023, 62, e202300756. |
| [38] | (a) Miralles, N.; Maza, R. J.; Fernández, E. Adv. Synth. Catal. 2018, 360, 1306. |
| [38] | (b) Nallagonda, R.; Padala, K.; Masarwa, A. Org. Biomol. Chem. 2018, 16, 1050. |
| [38] | (c) Wu, C.; Wang, J. Tetrahedron Lett. 2018, 59, 2128. |
| [38] | (d) Cuenca, A. B.; Fernández, E. Chem. Soc. Rev. 2021, 50, 72. |
| [38] | (e) Corro, M.; Salvado, O.; González, S.; Dominguez-Molano, P.; Fernández, E. Eur. J. Inorg. Chem. 2021, 2802. |
| [38] | (f) Jo, W.; Lee, J. H.; Cho, S. H. Chem. Commun. 2021, 57, 4346. |
| [38] | (g) Lee, Y.; Han, S.; Cho, S. H. Acc. Chem. Res. 2021, 54, 3917. |
| [38] | (h) Zhang, C.; Hu, W.; Morken, J. P. ACS Catal. 2021, 11, 10660. |
| [38] | (i) Paul, S.; Das, K. K.; Aich, D.; Manna, S.; Panda, S. Org. Chem. Front. 2022, 9, 838. |
| [39] | (a) Zhang, L.; Lovin?er, G. J.; Edelstein, E. K.; Szymaniak, A. A.; Chierchia, M. P.; Morken, J. P. Science 2016, 351, 70. |
| [39] | (b) Lovinger, G. J.; Aparece, M. D.; Morken, J. P. J. Am. Chem. Soc. 2017, 139, 3153. |
| [39] | (c) Chierchia, M.; Law, C.; Morken, J. P. Angew. Chem., Int. Ed. 2017, 56, 11870. |
| [39] | (d) Zhang, X.; Gao, C.; Morken, J. P. J. Am. Chem. Soc. 2023, 145, 16344. |
| [39] | (e) For a review, see: Namirembe, S.; Morken, J. P. Chem. Soc. Rev. 2019, 48, 3464. |
| [40] | (a) Davis, C. R.; Luvaga, I. K.; Ready, J. M. J. Am. Chem. Soc. 2021, 143, 4921. |
| [40] | (b) Davis, C. R.; Fu, Y.; Liu, P.; Ready, J. M. J. Am. Chem. Soc. 2022, 144, 16118. |
| [41] | (a) Ge, J.-F.; Zou, X.-Z.; Liu, X.-R.; Ji, C.-L.; Zhu, X.-Y.; Gao, D.-W. Angew. Chem., Int. Ed. 2023, 62, e202307447. |
| [41] | (b) Chen, A.; Qiao, Y.; Gao, D.-W. Angew. Chem., Int. Ed. 2023, 62, e202312605. |
| [42] | Jiang, X.-M.; Ji, C.-L.; Ge, J.-F.; Zhao, J.-H.; Zhu, X.-Y.; Gao, D.-W. Angew. Chem., Int. Ed. 2024, 63, e202318441. |
/
| 〈 |
|
〉 |
