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Paper | Special issue | Vol 62, No. 1, 2004, pp.251-262
Published online, 28th April, 2003
DOI: 10.3987/COM-03-S(P)2
Facial Selectivity in Nucleophilic Epoxidation of 3-Aryl-2-phosphonoacrylates Induced by the (-)-8-Phenylmenthyl Moiety as a Chiral Auxiliary

Shahnaz Begum, Md. Moshfiqur Rahman, Ryukichi Takagi, and Katsuo Ohkata*

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


Stereoselectivity was investigated in the epoxidation of (-)-8-phenylmenthyl E-3-aryl-2-phosphonoacrylates (2a-d) with hydrogen peroxide and potassium carbonate to give the corresponding epoxides (3a-d). The reaction of the E-isomeres gave the corresponding trans-epoxy derivatives with the moderately higher diastereoselectivity as the major diastereomers as compared with that of the cis isomers.