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Paper | Special issue | Vol 64, No. 1, 2004, pp.129-141
Published online, 16th April, 2004
DOI: 10.3987/COM-04-S(P)5
Influence of Polymerization Degree of Poly-L-leucine Catalyst and Substituent Effect on the Juliá-Colonna Asymmetric Epoxidation of Benzalacetophenones

Ryukichi Takagi, Shahnaz Begum, Akiko Siraki, Arata Yoneshige, Kin-ichirou Koyama, and Katsuo Ohkata*

*Department of Chemistry, Faculty of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

Abstract

The Juliá-Colonna asymmetric epoxidation reaction of substituted benzalacetophenone afforded the corresponding epoxide with high yield and high enantioselectivity, catalyzed by the specified length of poly-L-leucine (chain length n > 15). Poly-L-leucine catalysts have been prepared by the polymerization reaction of L-leucine-NCA with initiators (BnONa, n-BuNH2, H2O) and characterized by the MALDI-TOF Mass and IR analysis.