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For a comprehensive mechanistic rationale of the rhodium-catalyzed arylboronic acid conjugate addition to enones and a discussion of the crucial role of the protic source in the catalytic activity, see: Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
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note
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A ligand/rhodium ratio of 3/1 gave the optimum enantioselectivity. Using a lower ratio, the ee decreases slightly. This is probably due to competitive chelating properties of both substrate 1 and product 3. Using a higher ratio, dramatically lower activity was observed.
-
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59
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and the discussion in the Supporting Information
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Ligand (S)-L provided product (S)-3a. For determination of the absolute configuration of compound 3a, see: Barroso, S.; Blay, G.; Cardona, L.; Fernandez, I.; Garcia, B.; Pedro, J. R. J. Org. Chem. 2004, 69, 6821 and the discussion in the Supporting Information.
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