Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with new water-soluble chiral vicinal diamine as ligand.
[reaction: see text] 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 omega-bromo acetophenones was achieved, in which only formate displacement occurred when formic acid/triethylamine azeotrope was used as the hydrogen donor.
Ma
Yaping
Y
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, the Chinese Academy of Sciences, Chengdu 610041, China.
Liu
Hui
H
Chen
Li
L
Cui
Xin
X
Zhu
Jin
J
Deng
Jingen
J