RSS-Feed abonnieren
DOI: 10.1055/a-2532-4989
Advances in the 1,2-Metalate Rearrangement Chemistry of Alkenylboronates
Welch Foundation (I-1612).
Abstract
Synthetic methods that involve the formation of multiple bonds in a one-pot fashion have played a crucial role in organic chemistry. However, many features of these approaches are still limited, such as stereocontrol and chemoselectivity, especially when nonadjacent stereocenters are formed. Herein, we outlined our efforts in addressing these challenges by advancing the 1,2-metalate shift of alkenylboronic esters.
1 Introduction
2 1,2-Migration Strategy on Nitrogen-Containing Heterocyclic Substrates
3 Enantioselective Allylation with Metal(π-Allyl) Intermediates
4 Conclusion
Publikationsverlauf
Eingereicht: 19. Dezember 2024
Angenommen nach Revision: 04. Februar 2025
Accepted Manuscript online:
04. Februar 2025
Artikel online veröffentlicht:
21. März 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a Ruijter E. Orru R. V. A. 2013; 10: e15
- 1b Zarganes-Tzitzikas T, Dömling A. Org. Chem. Front. 2014; 1: 834
- 2 Matteson DS. Chem. Rev. 1989; 89: 1535
- 3a Wang H, Jing C, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2020; 59: 16859
- 3b Lovinger GJ, Morken JP. Eur. J. Org. Chem. 2020; 2362
- 3c Namirembe S, Morken JP. Chem. Soc. Rev. 2019; 48: 3464
- 3d Das KK, Panda S. Chem. Eur. J. 2020; 26: 14270
- 4a Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
- 4b Marshall CM, Federice JG, Bell CN, Cox PB, Njardarson JT. J. Med. Chem. 2024; 67: 11622
- 5a Bull JA, Mousseau JJ, Pelletier G, Charette AB. Chem. Rev. 2012; 112: 2642
- 5b Stout DM, Meyers A. Chem. Rev. 1982; 82: 223
- 6a Panda S, Coffin A, Nguyen QN, Tantillo DJ, Ready JM. Angew. Chem. Int. Ed. 2016; 55: 2205
- 6b Llaveria J, Leonori D, Aggarwal VK. J. Am. Chem. Soc. 2015; 137: 10958
- 7 McGettigan JE. Jr, Ready JM. Angew. Chem. Int. Ed. 2023; 62: e202216961
- 8a Pàmies O, Margalef J, Cañellas S, James J, Judge E, Guiry PJ, Moberg C, Bäckvall J.-E, Pfaltz A, Pericàs MA, Diéguez M. Chem. Rev. 2021; 121: 4373
- 8b Kazmaier U. Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis, Vol. 38. Springer Science & Business Media; Luxemburg: 2011
- 8c Arseniyadis S, Fournier J, Thangavelu S, Lozano O, Prevost S, Archambeau A, Menozzi C, Cossy J. Synlett 2013; 24: 2350
- 9 Trost BM, Crawley ML. Chem. Rev. 2003; 103: 2921
- 10 Panda S, Ready JM. J. Am. Chem. Soc. 2017; 139: 6038
- 11 Panda S, Ready JM. J. Am. Chem. Soc. 2018; 140: 13242
- 12a Tu H.-F, Yang P, Lin Z.-H, Zheng C, You S.-L. Nat. Chem. 2020; 12: 838
- 12b Cheng Q, Tu H.-F, Zheng C, Qu J.-P, Helmchen G, You S.-L. Chem. Rev. 2019; 119: 1855
- 12c Rossler SL, Petrone DA, Carreira EM. Acc. Chem. Res. 2019; 52: 2657
- 13 Davis CR, Luvaga IK, Ready JM. J. Am. Chem. Soc. 2021; 143: 4921
- 14 Feng J, Holmes M, Krische MJ. Chem. Rev. 2017; 117: 12564
- 15 Tran MK, Ready JM. Angew. Chem. Int. Ed. 2024; 63: e202407824
- 16 Davis CR, Fu Y, Liu P, Ready JM. J. Am. Chem. Soc. 2022; 144: 16118