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



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



Organic Letters 3(22): 3463-3466



[reaction: see text]. A novel application of the cinchona alkaloid derivative (DHQD)2PHAL in the osmium-catalyzed asymmetric dihydroxylation of olefins is presented. In a triple catalytic system using H2O2 as the terminal oxidant, the alkaloid ligand has a dual function in providing stereocontrol in the addition step and, via its N-oxidized form, acting as reoxidant for the in situ generated osmium(VI). The formation of the N-oxide is catalyzed by a biomimetic flavin.

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Accession: 046886264

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PMID: 11678683


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