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Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes
Authors:Bredikhin  A A  Strunskaya  E I  Novikova  V G  Azancheev  N M  Sharafutdinova  D R  Bredikhina  Z A
Institution:(1) A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation
Abstract:The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2-dioxaphospholanes. A synthesis of beta-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2-diols was proposed.
Keywords:enantioselective hydrolysis  chiral Co(salen)-catalyst  aryl glycidyl ethers  enantiomeric purity  31P NMR  3-aryloxypropane-1  2-diols  toliprolol  moprolol
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