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Synlett 1990; 1990(7): 421-423
DOI: 10.1055/s-1990-21114
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Use of Potassium Peroxodisulfate for Benzylic Oxidation and Oxidative Coupling of Benzoylacetates

Hiroshi Irie* , Jun Maruyama, Miki Shimada, Yong Zhang, Isao Kouno, Keiko Shimamoto, Yasufumi Ohfune
  • *Faculty of Pharmaceutical Sciences, Nagasaki University, Nagasaki 852, Japan
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Publication Date:
08 March 2002 (online)

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Oxidation of N-Boc-2-amino-3-(p-methoxyphenyl)-propane derivatives with potassium peroxodisulfate (K2S2O8) gave the cyclic carbamates with high threo selectivity. With the same reagent, 4-phenylbutanoic acids gave the corresponding lactones in fair yields by oxidation at the benzylic position, while the benzoylacetic acid esters afforded a mixture of threo (dl)- and erythro (meso)-2,3-bis(benzoyl)-1,4-butanedioic acid esters, both of which correspond to the lignan framework.

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