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note
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3(dme) and salen ligand in these ways showed inferior catalytic activity in terms of enantioselectivity (for examples, the oxidation of methyl phenyl sulfides with these Nb-4 complexes at room temperature showed 12-46% ee).
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12
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0001650799
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Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, Chap. 19
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For the recent reviews on asymmetric sulfoxidation, see: (a) Bolm, C.; Muniz, K.; Hildebrand, J. P. In Comprehensive Asymmetric Catalysis, Vol. II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Chap. 19. (b) Kagan, H. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000, Chap. 6C. Katsuki, T. Synlett 2003, 281.
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Ojima, I., Ed.; Wiley-VCH: New York, Chap. 6C
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For the recent reviews on asymmetric sulfoxidation, see: (a) Bolm, C.; Muniz, K.; Hildebrand, J. P. In Comprehensive Asymmetric Catalysis, Vol. II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Chap. 19. (b) Kagan, H. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000, Chap. 6C. Katsuki, T. Synlett 2003, 281.
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For examples of positive non-linear effect, see: (a) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877. (b) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (d) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (e) Soai, K.; Shibata, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 699. (f) Furuno, H.; Hanamoto, T.; Sugimoto, Y.; Inanaga, J. Org. Lett. 2000, 2, 49.
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For examples of positive non-linear effect, see: (a) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877. (b) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (d) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (e) Soai, K.; Shibata, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 699. (f) Furuno, H.; Hanamoto, T.; Sugimoto, Y.; Inanaga, J. Org. Lett. 2000, 2, 49.
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For examples of positive non-linear effect, see: (a) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877. (b) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (d) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (e) Soai, K.; Shibata, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 699. (f) Furuno, H.; Hanamoto, T.; Sugimoto, Y.; Inanaga, J. Org. Lett. 2000, 2, 49.
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For examples of positive non-linear effect, see: (a) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877. (b) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (d) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (e) Soai, K.; Shibata, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 699. (f) Furuno, H.; Hanamoto, T.; Sugimoto, Y.; Inanaga, J. Org. Lett. 2000, 2, 49.
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For examples of positive non-linear effect, see: (a) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877. (b) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. (d) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (e) Soai, K.; Shibata, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 699. (f) Furuno, H.; Hanamoto, T.; Sugimoto, Y.; Inanaga, J. Org. Lett. 2000, 2, 49.
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Furuno, H.1
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For the example of non-linear effect in metallosalen-catalyzed oxidation, see: Saito, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 8333.
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3(dme) (2.3 mg, 8.0 μmol) were dissolved in dichloromethane (2 mL) in a glovebox, and the solution was stirred for 2 h at room temperature. After addition of MS 4 Å (ca. 20 mg), the mixture was stirred for another 30 min. The mixture was taken out of the glovebox and cooled to -10°C under nitrogen. To this mixture were added methyl phenyl sulfide (12.0 μL, 0.10 mmol) and urea-hydrogen peroxide adduct (UHP) (10.5 mg, 0.11 mmol) successively, and the mixture was stirred for 2 days at the temperature. The mixture was directly chromatographed on silica gel (hexane-ethyl acetate = 1:1-1:19) to give methyl phenyl sulfoxide (12.4 mg, 88%). The enantiomeric excess of the sulfoxide was determined to be 86% ee by HPLC analysis using chiral stationary phase column (Daicel Chiralcel OD-H, hexane-i-PrOH = 9:1).
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