Osmium-catalyzed asymmetric dihydroxylation of olefins by H2O2 using a biomimetic flavin-based coupled catalytic system

Citation
Sy. Jonsson et al., Osmium-catalyzed asymmetric dihydroxylation of olefins by H2O2 using a biomimetic flavin-based coupled catalytic system, J AM CHEM S, 123(7), 2001, pp. 1365-1371
Citations number
64
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
00027863 → ACNP
Volume
123
Issue
7
Year of publication
2001
Pages
1365 - 1371
Database
ISI
SICI code
0002-7863(20010221)123:7<1365:OADOOB>2.0.ZU;2-P
Abstract
Selective cis-dihydroxylation of olefins with the aid of a triple catalytic system using H2O2 as the terminal oxidant has been developed. In this proc ess Os(VI) is recycled to Os(VIII) by a coupled electron-transfer-mediator system based on N-methylmorpholine and a biomimetic flavin, leading to a mi ld and selective electron transfer. Aliphatic, aromatic, and functionalized olefins were successfully cis-dihydroxylated, employing the triple catalyt ic system. The present biomimetic catalytic system works well in asymmetric dihydroxylation and gave optically active diols in good isolated yields an d high enantiomeric excesses (up to 99% ee).