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Paper | Special issue | Vol 30, No. 1, 1990, pp.517-535
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S45
Palladium(0) Catalyzes Reactions of 1,4-Epiperoxides

Masaaki Suzuki, Yoshihisa Oda, Nobuyuki Hamanaka, and Ryoji Noyori*

*Department of Chmistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan

Abstract

The Pd(PPh3)4 catalyzed reaction of 2,3-saturated and 2,3-unsaturated 1,4-epiperoxides proceeds by courses markedly different from those of the previously reported transition metal catalyses. The pd(0)-promoted reaction of 2,3-saturated epiperoxides gives the corresponding 4-hydroxy ketones and 1,4-diols as the major products. From 2,3-dedihydroepiperoxides are formed the corresponding 4-hydroxy enones, syn-1,2:3,4-diepoxides, and 1,4-diols. The results are interpreted in terms of competing Pd(0)/Pd(II) and Pd(0)/Pd(I) exchange mechanisms. Exposure of prostaglandin (PG) H2 methyl ester to Pd(PPh3)4 produces a mixture of methyl esters of PGD2, PGE2, PFF, and (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid.