82864-24-2Relevant articles and documents
OsO4?streptavidin: A tunable hybrid catalyst for the enantioselective cis-dihydroxylation of olefins
Koehler, Valentin,Mao, Jincheng,Heinisch, Tillmann,Pordea, Anca,Sardo, Alessia,Wilson, Yvonne M.,Knoerr, Livia,Creus, Marc,Prost, Jean-Christophe,Schirmer, Tilman,Ward, Thomas R.
supporting information; experimental part, p. 10863 - 10866 (2012/02/01)
Taking control: Selective catalysts for olefin dihydroxylation have been generated by the combination of apo-streptavidin and OsO4. Site-directed mutagenesis allows improvement of enantioselectivity and even inversion of enantiopreference in certain cases. Notably allyl phenyl sulfide and cis-β-methylstyrene were converted with unprecedented enantiomeric excess.
Synthesis of models of metabolites: Oxidation of variously substituted chromenes including acronycine, by a porphyrin catalytic system
Akagah, Bernardin,Estour, Francois,Verite, Philippe,Seguin, Elisabeth,Tillequin, Francois,Lafont, Olivier
, p. 1267 - 1272 (2007/10/03)
The influence of chemical neighbouring on oxidation of substituted 2,2-dimethylchromenes derivatives 5-8 by a biomimetic catalytic system was first studied. It was then applied to acronycine an anti-cancer drug in order to obtain in one single step oxidized products resulting from the reactivity of the 1,2-double bond in the pyranic D-ring. These 2,2-dimethylchromenes constitute the structural moiety responsible for the activity of acronycine. This oxidation showed the sensitivity of the ethylenic bond, leading to the formation of the corresponding epoxides, diols and/or ketoalcohol. In the case of 5-dimethylamino-2,2-dimethylchromene 8, the double bond was not sensitive to oxidation, but the N-methyl groups reacted to lead to the formamide derivative 16 and an imino-alcohol 17. This methodology applied to acronycine molecule 1, allowed to obtain in one step, two oxidized compounds, a trans-diol 3 and a ketoalcohol 4 under preparative conditions.
Osmium-Catalyzed Asymmetric Dihydroxylation of Cyclic Cis-Disubstituted Olefins
Wang, Zhi-Min,Kakiuchi, Kiyomi,Sharpless, K. Barry
, p. 6895 - 6897 (2007/10/02)
A new class of cis-disubstituted olefins has been found to give good enantioselectivities in the asymmetric dihydroxylation reaction using the standard PHAL and PYR ligands, all the olefins are conjugated, and the reacting double bond is endocyclic in a 5