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note
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Piperidine did not undergo α-metalation in Caulton's studies; see ref 3.
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11
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6044231417
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note
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Note that no arylation was observed at the α-methylene positions adjacent to the protected amine group in piperazine or oxygen in morpholine.
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12
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Examples of traditional methods for preparation of α-substituted cyclic imines: (a) Giovannini, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1989, 54, 228-234.
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0035823825
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For examples of direct C-H to C-C transformations at the α-methylene positions of N-protected pyrrolidines or tertiary amines, see: (a) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935-10941.
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An alternative mechanistic route from 27 to 29 may proceed via insertion of the metal into the C-H bond of the imine, followed by reductive elimination, (a) Ishiyama, T.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 12043-12044.
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