Methods for the synthesis of bicyclo[1.1.1]pentanes (BCPs) typically rely on the release of strain energy, but these routes cannot easily introduce substituents on the BCP bridges. Now, an intramolecular coupling gives access to multi-substituted BCPs, through the synthesis of bridge-substituted bicycloalkyl boronic esters.
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References
Locke, G. M., Bernhard, S. S. R. & Senge, M. O. Chem. Eur. J. 25, 4590–4647 (2019).
Auberson, Y. P. et al. ChemMedChem 12, 590–598 (2017).
Mondanaro, K. R., Dailey, W. P., Pal, R. & Wolff, S. Org. Synth. 75, 98 (1998).
Kanazawa, J. & Uchiyama, M. Synlett 30, 1–11 (2019).
Ma, X. & Nhat Pham, L. Asian J. Org. Chem. 9, 8–22 (2020).
Donnelly, K. & Baumann, M. Chem. Commun. 57, 2871–2874 (2021).
Anderson, J. M., Measom, N. D., Murphy, J. A. & Poole, D. L. Angew. Chem. Int. Ed. https://doi.org/10.1002/anie202106352 (2021).
Qin, T. et al. Nat. Chem. https://doi.org/10.1038/s41557-021-00786-z (2021).
Mykhailiuk, P. K. Org. Biomol. Chem. 17, 2839–2849 (2019).
Barluenga, J., Tomás-Gamasa, M., Aznar, F. & Valdés, C. Nat. Chem. 1, 494–499 (2009).
Yang, Y. et al. J. Am. Chem. Soc. 143, 471–480 (2021).
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Brocklehurst, C.E., Anderson, E.A. Building bridges. Nat. Chem. 13, 928–930 (2021). https://doi.org/10.1038/s41557-021-00784-1
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DOI: https://doi.org/10.1038/s41557-021-00784-1
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