Asymmetric Epoxidation Of Dihydronaphthalene With A Synthesized Jacobsen's Catalyst

2162 words - 9 pages

Asymmetric Epoxidation of Dihydronaphthalene with a Synthesized Jacobsen's CatalystJustin Lindsey12/08/96Chem 250 GGProfessor Tim HoytTA: Andrea EgansAbstract. 1,2 diaminocyclohexane was reacted with L-(+)-tartaric acid to yield (R,R)-1,2-diaminocyclohexane mono-(+)-tartrate salt. The tartrate salt was then reacted with potassium carbonate and 3,5-di-tert-butylsalicylaldehyde to yield (R,R)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine, which was then reacted with Mn(OAc)2*4H2O and LiCl to form Jacobsen's catalyst. The synthesized Jacobsen's catalyst was used to catalyze the epoxidation of dihydronaphthalene. The products of this reaction were isolated, and it was found that the product yielded 1,2-epoxydihydronaphthalene as well as naphthalene.IntroductionIn 1990, professor E.N. Jacobsen reported that chiral manganese complexes had the ability to catalyze the asymmetric epoxidation of unfunctionalized alkenes, providing enantiomeric excesses that regularly reaching 90% and sometimes exceeding 98% . The chiral manganese complex Jacobsen utilized was [(R,R)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato-(2-)]-manganese (III) chloride (Jacobsen's Catalyst).(R,R) Jacobsen's CatalystJacobsen's catalyst opens up short pathways to enantiomerically pure pharmacological and industrial products via the synthetically versatile epoxy function .In this paper, a synthesis of Jacobsen's catalyst is performed (Scheme 1). The synthesized catalyst is then reacted with an unfunctional alkene (dihydronaphthalene) to form an epoxide that is highly enantiomerically enriched, as well as an oxidized byproduct.Jacobsen's work is important because it presents both a reagent and a method to selectively guide an enantiomeric catalytic reaction of industrial and pharmacological importance. Very few reagents, let alone methods, are known to be able to perform such a function, which indicates the truly groundbreaking importance of Jacobsen's work.Experimental SectionGeneral Protocol. 99% L-(+)- Tartaric Acid, ethanol, dihydronaphthalene and glacial acetic acid were obtained from the Aldrich Chemical Company. 1,2 diaminocyclohexane (98% mix of cis/trans isomers) and heptane were obtained from the Acros Chemical Company. Dichloromethane and potassium carbonate were obtained from the EM Science division of EM Industries, Inc. Manganese acetate was obtained from the Matheson, Coleman and Bell Manufacturing Chemists. Lithium chloride was obtained form the JT Baker Chemical Co. Refluxes were carried out using a 100 V heating mantle (Glas-Col Apparatus Co. 100 mL, 90 V) and 130 V Variac (General Radio Company). Vacuum filtrations were performed using a Cole Parmer Instrument Co. Model 7049-00 aspirator pump with a Büchner funnel. For Thin Layer Chromatography (TLC) analysis, precoated Kodak chromatogram sheets (silica gel 13181 with fluorescent indicator) were used in an ethyl acetate/hexane (1:4) eluent. TLC's were visualized using a UVP Inc....

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