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Asymmetric Transfer Hydrogenation of Prochiral Ketones in Aqueous Media with New Water-Soluble Chiral Vicinal Diamine as Ligand

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journal contribution
posted on 10.05.2003, 00:00 by Yaping Ma, Hui Liu, Li Chen, Xin Cui, Jin Zhu, Jingen Deng
An easily accessible water-soluble chiral o-sulfonated 1,2-diphenylethlenediamine 2 and its mono-N-tosylated derivative 3 were synthesized for the first time. The ruthenium-complex-catalyzed reduction of prochiral ketones in aqueous media has been examined by using 3 as ligand and sodium formate as the source of hydrogen. The asymmetric transfer hydrogenation of ω-bromo acetophenones was achieved, in which only formate displacement occurred when formic acid/triethylamine azeotrope was used as the hydrogen donor.