Cross-coupling between a racemic secondary alkyl halide and an alkyl borane to produce an enantioenriched alkyl–alkyl product is one of the final substrate combinations to succumb to the synthetically powerful Suzuki–Miyaura methodology.
References
Denmark, S. E., Heemstra, J. R., Jr & Beutner, G. L. Angew. Chem. Int. Ed. 44, 4682–4698 (2005).
Zultanski, S. L. & Fu, G. C. J. Am. Chem. Soc. 133, 15362–15364 (2011).
Imao, D., Glasspoole, B. W., Laberge, V. S. & Crudden, C. M. J. Am. Chem. Soc. 131, 5024–5025 (2009).
Dreher, S. D., Dormer, P. G., Sandrock, D. L. & Molander, G. A. J. Am. Chem. Soc. 130, 9257–9259 (2008).
Ohmura, T., Awano, T. & Suginome, M. J. Am. Chem. Soc. 132, 13191–13193 (2010).
Lee, J. C. H., McDonald, R. & Hall, D. G. Nature Chem. 3, 894–899 10.1038/nchem.1150(2011).
Zhou, J. & Fu, G. C. J. Am. Chem. Soc. 126, 1340–1341 (2004).
Saito, B. & Fu, G. C. J. Am. Chem. Soc. 130, 6694–6695 (2008).
Owston, N. A. & Fu, G. C. J. Am. Chem. Soc. 132, 11908–11909 (2010).
Lu, Z., Wilsily, A. & Fu, G. C. J. Am. Chem. Soc. 133, 8154–8157 (2011).
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Glasspoole, B., Crudden, C. The final frontier. Nature Chem 3, 912–913 (2011). https://doi.org/10.1038/nchem.1210
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DOI: https://doi.org/10.1038/nchem.1210
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