Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2008;47(39):7520-2.
doi: 10.1002/anie.200802523.

Vanadium-catalyzed enantioselective desymmetrization of meso secondary allylic alcohols and homoallylic alcohols

Zhi Li  1 , Wei Zhang, Hisashi Yamamoto
Affiliations

Vanadium-catalyzed enantioselective desymmetrization of meso secondary allylic alcohols and homoallylic alcohols

Zhi Li et al. Angew Chem Int Ed Engl. 2008.

Abstract

Vanadium-catalyzed epoxidation has extended substrate scope. In addition to various bis-allylic alcohols, bis-homoallylic alcohols can also be desymmetrized using our Vanadium-Bis-hydroxamic acid complexes.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Asymmetric Epoxidation and Kinetic Resolution of Allylic and Homo-allylic Alcohols Catalyzed by Vanadium-BHA Complexes
Scheme 2
Scheme 2
Absolute Configuration Determination of 5a
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, Martin VS. Org React. 1996;48:1.Keith JM, Larrow JF, Jacobsen EN. Adv Synth Catal. 2001;343:5.Adam W, Malisch W, Roschmann KJ, Saha-Möller CR, Schenk WA. J Organomet Chem. 2002;661:3.Shi Y. Acc Chem Res. 2004;37:488.Shi Y, Frohn M. Synthesis. 2000;14:1979.

    1. Zhang W, Basak A, Kosugi Y, Hoshino Y, Yamamoto H. Angew Chem Int Ed. 2005;44:4389. - PubMed
    1. Zhang W, Yamamoto H. J Am Chem Soc. 2007;129:286. - PMC - PubMed

    1. For studies toward desymmetrization via olefin epoxidation, see: Hatakeyama S, Sakurai K, Takano S. J Chem Soc, Chem Commun. 1985:1759.Schreiber SL, Schreiber TS, Smith DB. J Am Chem Soc. 1987;109:1525.Schreiber SL, Goulet MT, Schulte G. J Am Chem Soc. 1987;109:4718.Kramer R, Berkenbusch T, Brückner R. Adv Synth Catal. 2008;350:1131.

    1. For synthetic applications of desymmetrization via Sharpless Epoxidation, see: Kobayashi Y, Kato N, Shimazaki T, Sato F. Tetrahedron Letters. 1988;29:6297.Hatakeyama S, Sakurai K, Numata H, Ochi N, Takano S. J Am Chem Soc. 1988;110:5201.Smith DB, Zhaoyin W, Schreiber SL. Tetrahedron. 1990;46:4793.Berkenbusch T, Brückner R. Synlett. 2003:1813.Kramer R, Brückner R. Synlett. 2006:0033.

Publication types

LinkOut - more resources