Osmium-catalyzed asymmetric dihydroxylation of olefins by H2O2; Dual role of the cinchona alkaloid ligand

Authors
Jonsson, SY Adolfsson, H Backvall, JE
Citation
Sy. Jonsson et al., Osmium-catalyzed asymmetric dihydroxylation of olefins by H2O2; Dual role of the cinchona alkaloid ligand, ORG LETT, 3(22), 2001, pp. 3463-3466
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
22
Year of publication
2001
Pages
3463 - 3466
Database
ISI
SICI code
1523-7060(20011101)3:22<3463:OADOOB>2.0.ZU;2-4
Abstract
[GRAPHICS] A novel application of the cinchona alkaloid derivative (DHQD)(2)PHAL in th e osmium-catalyzed asymmetric dihydroxylation of olefins is presented. In a triple catalytic system using H2O2 as the terminal oxidant, the alkaloid l igand has a dual function in providing stereocontrol in the addition step a nd, via its IV-oxidized form, acting as reoxidant for the in situ generated osmium(VI). The formation of the N-oxide is catalyzed by a biomimetic flav in.