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Bellus, D., Ley, S. V., Noyori, R., Regitz, M., Schaumann, E., Shinkai, I., Thomas, E., J., Trost, B. M., Eds.; Georg Thieme Verlag: Stuttgart
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For a review on silicon enolates, see: Kobayashi, S.; Manabe, K.; Ishitani, H.; Matsuo, J. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformation; Bellus, D., Ley, S. V., Noyori, R., Regitz, M., Schaumann, E., Shinkai, I., Thomas, E., J., Trost, B. M., Eds.; Georg Thieme Verlag: Stuttgart, 2002; Vol. 4, p 317.
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For reviews on asymmetric aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352.
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Jacobsen, E. N., Pflatz, A., Yamamoto, H., Eds.; Springer; Heidelberg
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(b) Carreira, E. M. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pflatz, A., Yamamoto, H., Eds.; Springer; Heidelberg, 1999; Vol. 3, p 998.
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Carreira, E.M.1
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Trioxane was used as a formaldehyde surrogate: Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
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For hydroxymethylation of a silicon enolate in aqueous media without any catalysts, see: (b) Lubineau, A.; Meyer, E. Tetrahedron 1988, 44, 6065.
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Manabe, K.; Ishikawa, S.; Hamada, T.; Kobayashi, S. Tetrahedron 2003, 59, 10439.
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Ozawa, N.; Wadamoto, M.; Ishihara, K.; Yamamoto, H. Synlett 2003, 2219.
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(b) Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227.
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(a) Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205.
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(b) Bohn, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber. 1992, 125, 1169.
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2,6-Di-tert-butylpyridine was used as an additive for Lewis acid-catalyzed aldol reactions. For example: (a) Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4275.
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(b) Hamada, T.; Manabe, K.; Ishikawa, S.; Nagayama, S.; Shiro, M.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 2989.
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19
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33751157649
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Also see: ref 10b
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It is also noteworthy that water is essential in this reaction. To see the effects of water in this catalytic system, we performed an asymmetric aldol reaction of benzaldehyde where anhydrous conditions were easy to access. While the reaction of benzaldehyde with 2 in H20/DME (1:9) at -20 °C for 21 h proceeded smoothly with good yield (76%) and modest selectivity (syn/anti = 78/22, 59% ee (syn)) using 10 mol % of the chiral Sc catalyst, the reaction in DME without water did not proceed at all (-20 °C, 24 h). This result indicates that water plays an important role for the catalytic activity in this system. For effects of water in rare earth metal triflate-catalyzed aldol reactions, see: Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590. Also see: ref 10b.
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Kobayashi, S.1
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20
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4644373280
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note
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3: 22 h, 75% yield, 83% ee).
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21
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0035814327
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3-complexes with chiral ligands: (a) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 12095.
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(b) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
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(a) Baliri, P. L.; Catelani, G.; Giori, R.; Mastrorilli, E. Enantiomer 1998, 3, 357.
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(b) Miyaoka, H.; Kajiwara, Y.; Hara, M.; Suma, A.; Yamada, Y. Tetrahedron: Asymmetry 1999, 10, 3189.
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25
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0001567028
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For reviews on catalytic asymmetric carbon-carbon bond-forming reactions in aqueous media, see: (a) Sinou, D. Adv. Synth. Catal. 2002, 344, 221.
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Sinou, D.1
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