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Takemoto, Y.4
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75
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39549091935
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For selected examples of catalytic asymmetric Mannich reactions with 1,3-dicarbonyl compounds generating tertiary stereocenters, see
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(f) Chen, Z.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 2170. For selected examples of catalytic asymmetric Mannich reactions with 1,3-dicarbonyl compounds generating tertiary stereocenters, see:
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J. Am. Chem. Soc
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Chen, Z.1
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(h) Lou, S.; Taoka, B. M.; Ting, A.; Schaus, S. E. J. Am. Chem. Soc. 2005, 127, 11256.
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J. Am. Chem. Soc
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(i) Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048.
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(j) Sasamoto, N.; Dubs, C.; Hamashima, Y.; Sodeoka, M. J. Am. Chem. Soc. 2006, 128, 14010.
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80
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56249102432
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and references therein. A general review on enantioselectivity reversal using a single chiral source, see
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A general review on enantioselectivity reversal using a single chiral source, see: Tanaka, T.; Hayashi, M. Synthesis 2008, 3361, and references therein.
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Synthesis
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Tanaka, T.1
Hayashi, M.2
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81
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33744830047
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A notable example of an asymmetric catalyst exhibiting sharp enantioswitching, depending on the assembly state of the catalyst, see
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A notable example of an asymmetric catalyst exhibiting sharp enantioswitching, depending on the assembly state of the catalyst, see: Kato, N.; Mita, T.; Kanai, M.; Therrien, B.; Kawano, M.; Yamaguchi, K.; Danjo, H.; Sei, Y.; Sato, A.; Furusho, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6768.
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Sei, Y.8
Sato, A.9
Furusho, S.10
Shibasaki, M.11
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0034807976
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The rate acceleration suggested the involvement of hydrogen-bonding to promote the reaction and enhance the stereodiscrimination at the transition state. The hydrogen-bonding in peptide-based catalysts is well-documented, see: (a) Copeland, G. T, Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496
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The rate acceleration suggested the involvement of hydrogen-bonding to promote the reaction and enhance the stereodiscrimination at the transition state. The hydrogen-bonding in peptide-based catalysts is well-documented, see: (a) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496.
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83
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(b) Sculimbrene, B. R.; Morgan, A. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 11653.
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52449099149
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and references therein
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(c) Jakobsche, C. E.; Peris, G.; Miller, S. J. Angew. Chem., Int. Ed. 2008, 47, 6707, and references therein.
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Jakobsche, C.E.1
Peris, G.2
Miller, S.J.3
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85
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85069284426
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We cannot exclude the possibility that a higher ligand exchange rate of Er would contribute to enhanced catalyst turnover
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We cannot exclude the possibility that a higher ligand exchange rate of Er would contribute to enhanced catalyst turnover.
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86
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85069280018
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See Supporting Information for details
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See Supporting Information for details.
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87
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85069280497
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The reaction with the opposite order of metal source addition did not show functional changes as expected from the results of the previous section. Details are shown in Supporting Information
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The reaction with the opposite order of metal source addition did not show functional changes as expected from the results of the previous section. Details are shown in Supporting Information.
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