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Jacobsen

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Synthesis of (R,R) Jacobsen’s Salen(Co) Catalyst and Product Analysis of Hydrolytic Kinetic Resolution of Phenyl Glycidyl Ether
Grace Sun, Caralyn Takata, Elisabeth Young
Thursday Evening Chem 250 Laboratory, Fall 2010

Abstract: It was discovered by Eric N. Jacobsen that the chiral Jacobsen’s Salen(Co) complex 6 is effective in acting as a catalyst for the hydrolytic kinetic resolution (HKR) for regioselecting epoxides. The complex is prepared in four steps. A mixture of 1,2-diaminocyclohexane isomers was selectively crystallized to form 1,2-diaminocyclohexane L-tartrate salt. The salene ligand was formed by reacting 3,5-di-tert-butyl-2-hydroxybenzaldehyde with 1,2-diaminocyclohexane. The Salen(Co) complex was formed by treating the salen ligand with cobalt(II) acetate. Finally, the catalyst was formed by processing the ligand through aerobic oxidation in the presence of acetic acid. The catalyst was used to resolve phenyl glycidyl ether and the diol 9 and epoxide 8 were separated by flash chromatography. The products were characterized through chiral HPLC, IR, H-NMR, and polarimitry tests. HPLC spectrum showed that the catalyst had successfully yielded enantiomerically pure diol 9 and epoxide 8 molecules with 8 being resolved to 99.4% ee and 9 with 93.8% ee. Although (R,R) and (S,S) Jacobsen’s Salen(Co) Catalysts select for different enantiomers of epoxides, reactions utilizing either catalyst resulted in similar yields, within 1%. The data collected is useful in showing that the HKR reaction was highly effective in regioselecting the respective epoxides.

Introduction Despite their opposite structures, enantiomers posses identical chemical properties and only differ by their physiological activity in chiral environments, one being the human body.1 This is a major concern for the pharmaceutical community because it is possible for one enantiomer of a…...

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