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Selected examples: (a) Hasegawa, Y.; Watanabe, M.; Gridnev, I. D.; Ikariya, T. J. Am. Chem. Soc. 2008, 130, 2158.
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Metal-catalyzed Conia-ene reactions: (a) Au: Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
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Metal-catalyzed Conia-ene reactions: (a) Au: Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
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(b) Ni: Gao, Q.; Zheng, B.-F.; Li, J.-H.; Yang, D. Org. Lett. 2005, 7, 2185.
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(c) Cu: Bouyssi, D.; Monteiro, N.; Balme, G. Tetrahedron Lett. 1999, 40, 1297.
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67649911306
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We postulate that the Lewis acidity of the metal-ion complex was poisoned by strong ligation to the thiourea
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We postulate that the Lewis acidity of the metal-ion complex was poisoned by strong ligation to the thiourea.
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27
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67649933092
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At high copper(I) loadings, saturation of the bridgehead nitrogen presumably reduces the amount of Brønsted base required for enolate formation
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At high copper(I) loadings, saturation of the bridgehead nitrogen presumably reduces the amount of Brønsted base required for enolate formation.
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28
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67649905062
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The reaction was quenched and analyzed after 3 h (25% conversion, E/Z = 94:6) to minimize the extent of Cu(I)-promoted H/D exchange processes in 5 prior to cyclization.
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The reaction was quenched and analyzed after 3 h (25% conversion, E/Z = 94:6) to minimize the extent of Cu(I)-promoted H/D exchange processes in 5 prior to cyclization.
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