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

doi:10.1055/s-1990-21114

Synlett 1990; 1990(7): 421-423
DOI: 10.1055/s-1990-21114

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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.

PDF (140 kb)