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(a) Matsuda, T.; Makino, M.; Murakami, M. Org. Lett. 2004, 6, 1257.
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For analogous reaction creating a chiral center by β-carbon elimination from Pd(II) cyclobutanolate. see: Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862.
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For recent examples of asymmetric synthesis of 3,3-disubstituted 1-indanones, see: (a) Shintani, R.; Hayashi, T. Org. Lett. 2005, 7, 2071.
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33746910428
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note
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DPPB = 1,4-bis(diphenylphosphino)butane.
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14
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1342302388
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For recent examples of synthetic application of β-carbon elimination with transition metal cyclobutanolates, see: (a) Pd: Nishimura, T.; Uemura, S. Synlett 2004, 201.
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Nishimura, T.1
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(b) Ni: Murakami, M.; Ashida, S.; Matsuda, T. J. Am. Chem. Soc. 2005, 127, 6932.
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33746903783
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note
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Deuterium labeling experiments revealed that 1,4- and 1,3-Rh shifts occurred prior to protonolysis. See the Supporting Information for further details. (Diagram Presented)
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17
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1942469490
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Dihedral angles (θ) of free phosphines: SEGPHOS 67.2°; MeO-BIPHEP 72.3°; BINAP 86.2°. Jeulin, S.; Duprat de Paule, S.; Ratovelo-manana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5799.
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Dellis, P.6
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and references therein
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ent-13: (c) Srikrishna, A.; Babu, N. C.; Rao, M. S. Tetrahedron Lett. 2004, 60, 2125 and references therein.
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