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Osmium-Catalyzed Asymmetric Dihydroxylation of Olefins by H2O2 Using a Biomimetic Flavin-Based Coupled Catalytic System

Sandra Y. Jonsson, Katarina Färnegårdh and Jan-E. Bäckvall

*Department of Chemistry, Tsing Hua University, Hsinchu, 30013 Taiwan

S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc., 2001, 123, 1365-1371.

DOI: 10.1021/ja0035809


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Abstract

Os(VI) can be recycled to Os(VIII) by a coupled electron-transfer-mediator system based on N-methylmorpholine and a biomimetic flavin, leading to a mild and selective electron transfer. Aliphatic, aromatic, and functionalized olefins were successfully cis-dihydroxylated. The present biomimetic catalytic system also works well in Sharpless asymmetric dihydroxylation.

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proposed catalytic cycle



Key Words

Upjohn Dihydroxylation, hydrogen peroxide


ID: J48-Y2001