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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:

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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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 0C 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.

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W. Zhang, H. Yamamoto, J. Am. Chem. Soc., 2007, 129, 286-287.

Novel α-Amino Acid-Based Hydroxamic Acid Ligands for Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols

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