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Catalytic Asymmetric Epoxidation of α,β-Unsaturated Esters Using an Yttrium-Biphenyldiol Complex

Hiroyuki Kakei, Riichiro Tsuji, Takashi Ohshima and Masakatsu Shibasaki*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku Tokyo 113-0033, Japan, Email:

H. Kakei, R. Tsuji, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc., 2005, 127, 8962-8963.

DOI: 10.1021/ja052466t


A catalytic asymmetric epoxidation reaction of various α,β-unsaturated esters via a conjugate addition of an oxidant using an yttirium-chiral biphenyldiol catalyst yielded the corresponding α,β-epoxy esters in up to 97% yield and 99% ee.

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Key Words

Epoxidation, Epoxy Esters, tert-Butylhydroperoxide

ID: J48-Y2005-2390