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. 2007 Jan 17;129(2):286-7.
doi: 10.1021/ja067495y.

Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols

Wei Zhang  1 , Hisashi Yamamoto
Affiliations

Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols

Wei Zhang et al. J Am Chem Soc. .

Erratum in

  • J Am Chem Soc. 2007 Apr 25;129(16):5298
No abstract available

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Figures

Scheme 1
Scheme 1
Asymmetric epoxidation of allylic alcohols and homoallylic alcohols by vanadium and BHA complex.
Scheme 2
Scheme 2
Kinetic resolution of homoallylic alcohols.
See this image and copyright information in PMC

References

    1. For recent reviews, see Katsuki T. In: Comprehensive Asymmetric Catalysis. Jacobsen EN, Pfaltz A, Yamamoto H, editors. Vol. 2. Springer; Berlin: 1999. p. 621.Katsuki T, Ojima I. Org React. 1996;48:1.Keith JM, Larrow JF, Jacobsen EN. Adv Synth Catal. 2001;343:5.Adam W, Saha-Möller CR, Ganeshpure PA. Chem Rev. 2001;101:3499.Adam W, Malisch W, Roschmann KJ, Saha-Möller CR, Schenk WA. J Organomet Chem. 2002;661:3.Lattanzi A, Scettri A. J Organomet Chem. 2006;691:2072.Shi Y. Acc Chem Res. 2004;37:488.Shi Y, Frohn M. Synthesis. 2000;14:1979.

    1. Katsuki T, Sharpless KB. J Am Chem Soc. 1980;102:5974.
    2. Rossiter BE, Sharpless KB. J Org Chem. 1984;49:3707.
    3. Gao Y, Hanson RM, Klunder JM, Ko SY, Masamune H, Sharpless KB. J Am Chem Soc. 1987;109:5765.

    1. For Zr catalyzed epoxidation of homoallylic alcohols, see Ikegami S, Katsuki T, Yamaguchi M. Chem Lett. 1987:83.Okashi T, Murai N, Onaka M. Org Lett. 2003;5:85.

    1. Makita N, Hoshino Y, Yamamoto H. Angew Chem Int Ed. 2003;42:941. - PubMed

    1. For a related epoxidation of allylic alcohols, see Murase Y, Hoshino Y, Oishi M, Yamamoto H. J Org Chem. 1999;64:338.Hoshino Y, Murase N, Oishi M, Yamamoto H. Bull Chem Soc Jpn. 2000;73:1653.Hoshino Y, Yamamoto H. J Am Chem Soc. 2000;122:10452.

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