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Recently Katsuki developed a chiral salen/Ru catalyst (2 mol%) that promotes aerobic oxidation of meso-diols to give lactols in 59-67% ee in 49-66% yield. See: Shimizu, H.; Nakata, K.; Katsuki, T. Chem. Lett. 2002, 1080-1081 Asymmetric oxidative lactonization of meso-diols using a chiral amino phosphine/Ru catalyst has been reported. See: Ito, M.; Osaku, A.; Ikariya, T. The 84th Annual Meeting of the Chemical Society of Japan, Tokyo, March 2002, Abstr., No. 3 G4-14.
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For other metal-catalyzed desymmetrization of meso-diols, see: (a) Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593-1595; (b) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476; (c) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
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For other metal-catalyzed desymmetrization of meso-diols, see: (a) Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593-1595; (b) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476; (c) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
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For other metal-catalyzed desymmetrization of meso-diols, see: (a) Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593-1595; (b) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476; (c) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
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26
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85031227438
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note
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3), (2S,3R)).
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27
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85031219345
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The reaction at 0°C gave only 10% yield after 24 h without greatly improving the enantioselectivity (75% ee).
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The reaction at 0°C gave only 10% yield after 24 h without greatly improving the enantioselectivity (75% ee).
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28
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0022998225
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Hall S.E., Han W.C., Haslanger M.F., Harris D.N., Ogletree M.L. J. Med. Chem. 29:1986;2335-2347.
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Ogletree, M.L.5
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29
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85031217943
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The use of other ligands such as (R)-valinol or (1R,2S)-cis-1-amino-2-indanol also gave lower ee with moderate yield
-
The use of other ligands such as (R)-valinol or (1R,2S)-cis-1-amino-2-indanol also gave lower ee with moderate yield.
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30
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0027723320
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Hamilton G.S., Huang Z., Yang X.J., Patch R.J., Narayanan B.A., Ferkany J.W. J. Org. Chem. 58:1993;7263-7270.
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