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0345529038
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For the other recent reports on the asymmetric reactions of imines with silicon enolates in water-containing solvents, see: (a) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III. J. Org. Chem. 2003, 68, 9624.
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14
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For reports on the catalytic asymmetric carbon-carbon bond-forming reactions using acylhydrazones, see: (a) Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131.
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(c) Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 6610.
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(d) Hamada, T.; Manabe, K.; Kobayashi, S. Angew. Chem., Int. Ed. 2003, 42, 3927.
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Schiessl, H.W.1
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21
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3042540262
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note
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4
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22
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3042672474
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note
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In the reactions using the silyl enol ethers derived from α-monosubstituted carbonyl compounds, 1b was used instead of 1c, because 1b gave higher selectivities (Table 2, entry 9) in the reactions using propiophenone-derived silyl enol ether than 1c (86%, syn/anti = 94/6, 92% ee).
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24
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0003398408
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Holland, P. M., Rubingh, D. N., Eds.; American Chemical Society: Washington, DC
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(b) Mixed Surfactant Systems; Holland, P. M., Rubingh, D. N., Eds.; American Chemical Society: Washington, DC, 1992.
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Mixed Surfactant Systems
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25
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0003938051
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Cramer, C. J., Truhlar, D. G., Eds.; American Chemical Society: Washington, DC
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(c) Structure and Reactivity in Aqueous Solution; Cramer, C. J., Truhlar, D. G., Eds.; American Chemical Society: Washington, DC, 1994.
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Structure and Reactivity in Aqueous Solution
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26
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0004130340
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Sabatini, D. A., Knox, R. C., Harwell, J. H., Eds.; American Chemical Society: Washington, DC
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(d) Surfactant-Enhanced Subsurface Remediation; Sabatini, D. A., Knox, R. C., Harwell, J. H., Eds.; American Chemical Society: Washington, DC, 1994.
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(1994)
Surfactant-Enhanced Subsurface Remediation
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28
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3042540263
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note
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When CTAB (5 mol %) was used in the reaction in Table 1, entry 5, remarkable acceleration of the reaction was not observed, and the ee was decreased (56% yield, 92% ee for 5 h).
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29
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0037157202
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(a) Manabe, K.; Mori, Y.; Wakabayashi, T.; Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 5640.
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Kobayashi, S.5
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0004253266
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(b) Kobayashi, S.; Mori, Y.; Nagayama, S.; Manabe, K. Green Chem. 1999, 175.
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Green Chem.
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Kobayashi, S.1
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0030913328
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(c) Kobayashi, S.; Wakabayashi, T.; Nagayama, S.; Oyamada, H. Tetrahedron Lett. 1997, 26, 4559.
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Kobayashi, S.1
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Nagayama, S.3
Oyamada, H.4
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3042525957
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note
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tBu, CPB (2 mol %) 38% yield, syn/anti = 10/90, 94% ee (anti)).
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33
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3042525956
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note
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tBu groups.
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34
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0037420331
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Although diastereoselectivities were not as high as the present reactions, stereospecificities were also observed in the asymmetric Mannich-type reactions. See: Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507.
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J. Am. Chem. Soc.
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Kobayashi, S.1
Matsubara, R.2
Nakamura, Y.3
Kitagawa, H.4
Sugiura, M.5
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