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b) J. A. Wilkinson, S. B. Rossington, S. Ducki, J. Leonard, N. Hussain, Tetrahedron: Asymmetry 2004, 15, 3011;
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33748778802
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Recent progress in the metal-catalyzed hydroarylation of styrene derivatives has allowed access to 1,1-diarylalkanes in racemic form, see, for example: a H.-B. Sun, B. Li, R. Hua, Y. Yin, Chem. 2006, 4231;
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Recent progress in the metal-catalyzed hydroarylation of styrene derivatives has allowed access to 1,1-diarylalkanes in racemic form, see, for example: a) H.-B. Sun, B. Li, R. Hua, Y. Yin, Eur. J. Org. Chem. 2006, 4231;
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b) M. Rueping, B. J. Nachtsheim, T. Scheidt, Org. Lett. 2006, 8, 3717;
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37349000125
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For the gold standard in the asymmetric reduction of unfunctionalized C=C bonds, see: a S. Bell, B. Wuestenberg, S. Kaiser, F. Menges, A. Pfaltz. Science 2006, 311, 5761;
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For the "gold standard" in the asymmetric reduction of unfunctionalized C=C bonds, see: a) S. Bell, B. Wuestenberg, S. Kaiser, F. Menges, A. Pfaltz. Science 2006, 311, 5761;
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The optically active diene ligand, [(1R,4R,8R)-5- benzyl-8-methoxy-1,8-dimethyl-2-(2′-methylpropyl)bicyclo[2.2.2]octa-2, 5-diene] and its enantiomer are commercially available from Aldrich under the name dolefin.
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The optically active diene ligand, [(1R,4R,8R)-5- benzyl-8-methoxy-1,8-dimethyl-2-(2′-methylpropyl)bicyclo[2.2.2]octa-2, 5-diene] and its enantiomer are commercially available from Aldrich under the name "dolefin".
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0003995267
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For a recent review of Pd-catalyzed decarbonylations, see:, Ed, E. Negishi, Wiley, New York
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For a recent review of Pd-catalyzed decarbonylations, see: J. Tsuji in Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley, New York, 2002.
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Handbook of Organopalladium Chemistry for Organic Synthesis
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Tsuji, J.1
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33646841336
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For examples of recent applications of Ir-catalyzed decarbonylations, see: a F. Y. Kwong, H. W. Lee, W. H. Lam, L. Qiu, A. S. C. Chan, Tetrahedron: Asymmetry 2006, 17, 1238;
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For examples of recent applications of Ir-catalyzed decarbonylations, see: a) F. Y. Kwong, H. W. Lee, W. H. Lam, L. Qiu, A. S. C. Chan, Tetrahedron: Asymmetry 2006, 17, 1238;
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For examples of Rh-catalyzed decarbonylation methods, see: a C. M. Beck, S. E. Rathmill, Y. J. Park, J. Chen, R. H. Crabtree, L. M. Liable-Sands, A. L. Rheingold, Organometallics 1999, 18, 5311;
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For examples of Rh-catalyzed decarbonylation methods, see: a) C. M. Beck, S. E. Rathmill, Y. J. Park, J. Chen, R. H. Crabtree, L. M. Liable-Sands, A. L. Rheingold, Organometallics 1999, 18, 5311;
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37349102201
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The optically active aldehydes 1a, 1b, 1d, and 1g have been prepared previously. For corresponding ee values and experimental data, see reference [9]. In all other cases, see the Supporting Information.
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The optically active aldehydes 1a, 1b, 1d, and 1g have been prepared previously. For corresponding ee values and experimental data, see reference [9]. In all other cases, see the Supporting Information.
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1H NMR spectra of the crude reaction mixtures.
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1H NMR spectra of the crude reaction mixtures.
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37349088374
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It was found that stringent removal of methanol was necessary to minimize the oxidative Tishchenko-like coupling of the alcohol and the intermediate aldehyde 1a, generating methyl ester by-products
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It was found that stringent removal of methanol was necessary to minimize the oxidative Tishchenko-like coupling of the alcohol and the intermediate aldehyde 1a, generating methyl ester by-products.
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0037123291
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For seminal reports, see: a
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For seminal reports, see: a) T. Morimoto, K. Fuji, K. Tsutsumi, K. Kakiuchi, J. Am. Chem. Soc. 2002, 124, 3806;
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0037131281
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b) T. Shibata, N. Toshida, K. Takagi, J. Org. Chem. 2002, 67, 7446;
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c) T. Shibata, N. Toshida, K. Takagi, Org. Lett. 2002, 4, 1619.
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T. Morimoto, M. Fujioka, K. Fuji, K. Tsutsumi, K. Kakiuchi, J. Organomet. Chem. 2007, 692, 625.
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Morimoto, T.1
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37349073628
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The reaction was performed with (+)-dolefin ligand [(1R,4R, 8R)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2′-methyl-propyl)-bicyclo[2. 2.2]octa-2,5-diene].
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The reaction was performed with (+)-dolefin ligand [(1R,4R, 8R)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2′-methyl-propyl)-bicyclo[2. 2.2]octa-2,5-diene].
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41
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37349002257
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The reaction was performed with epi-(-)-dolefin ligand [(1S,4S,8R)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2′- methyl-propyl)-bicyclo[2.2.2]octa-2,5-diene].
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The reaction was performed with epi-(-)-dolefin ligand [(1S,4S,8R)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2′- methyl-propyl)-bicyclo[2.2.2]octa-2,5-diene].
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