Enantioselective Epoxidation of Allylic Alcohols by a Chiral Complex of Vanadium: An Effective Controller System and a Rational Mechanistic Model
Wei Zhang, Arindrajit Basak, Yuji Kosugi, Yujiro Hoshino, Hisashi Yamamoto*
*Department of Chemistry, The University of Chicago, 5735 South Ellis
Avenue, Chicago, IL 60637, USA, Email: yamamoto
uchicago.edu
W. Zhang, A. Basak, Y. Kosugi, Y. Hoshino, H. Yamamoto, Angew. Chem. Int. Ed., 2005, 44, 4389-4391.
DOI: 10.1002/anie.200500938
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Abstract
A new catalytic system for the asymmetric epoxidation of allylic alcohols has been developed featuring high enantioselectivity for Z olefins, catalyst loading of less than 1 mol%, reaction temperatures of 0°C to room temperature over a shorter time, use of aqueous tert-butyl hydroperoxide (TBHP) instead of anhydrous TBHP as an achiral oxidant, and simple workup procedures for small expoxy alcohols.
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Tungsten-Catalyzed Asymmetric Epoxidation of Allylic and Homoallylic Alcohols with Hydrogen Peroxide
C. Wang, H. Yamamoto, J. Am. Chem. Soc., 2014, 136, 1222-1225.
Vanadium-Catalyzed Asymmetric Epoxidation of Homoallylic Alcohols
W. Zhang, H. Yamamoto, J. Am. Chem. Soc., 2007, 129, 286-287.
Y. Hoshino, H. Yamamoto, J. Am. Chem. Soc., 2000, 122, 10452-10453.
Key Words
asymmetric catalysis, chirality, epoxidation, ligand design, vanadium, cumene hydroperoxide, tert-butyl hydroperoxide
ID: J06-Y2005-890
