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

Yujiro Hoshino and Hisashi Yamamoto*

*Graduate School of Engineering, Nagoya University CREST, Japan Science and Technology Corporation (JST) Furo-cho, Chikusa, Nagoya 464-8603, Japan, Email: yamamotouchicago.edu

Y. Hoshino, H. Yamamoto, J. Am. Chem. Soc., 2000, 122, 10452-10453.

DOI: 10.1021/ja002602o

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Abstract

Chiral amino acid-based hydroxamic acids can be effective asymmetric catalysts for the epoxidation of allylic alcohols, especially disubstituted allylic alcohols. The mild reaction conditions, e.g., reasonable temperature, low degree of catalyst loading, and halogen-free solvent, extend the scope of this process.

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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.

Enantioselective Epoxidation of Allylic Alcohols by a Chiral Complex of Vanadium: An Effective Controller System and a Rational Mechanistic Model

W. Zhang, A. Basak, Y. Kosugi, Y. Hoshino, H. Yamamoto, Angew. Chem. Int. Ed., 2005, 44, 4389-4391.

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Key Words

epoxidation, vanadium, tert-butyl hydroperoxide

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ID: J48-Y2000