Asymmetric Epoxidation of Dihydronaphthalene with a Synthesized Jacobsen's Catalyst

Asymmetric Epoxidation of Dihydronaphthalene with a Synthesized Jacobsens Catalyst Justin Lindsey 12/08/96 Chem 250 GG Professor Tim Hoyt TA: Andrea Egans Abstract. 1,2 diaminocyclohexane was reacted with L-(+)-tartaric acid to apply (R,R)-1,2-diaminocyclohexane mono-(+)-tartrate salt. The tartrate salt was then reacted with honey oil carbonate and 3,5-di-tert-butylsalicylaldehyde to retort (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 design Jacobsens atom smasher. The synthesized Jacobsens throttle valve was use to catalyze the epoxidation of dihydronaphthalene. The products of this chemical reaction were isolated, and it was found that the product yielded 1,2- epoxy resindihydronaphthalene as soundly as naphthalene. Introduction         In 1990, professor E.N. Jacobsen reported that chiral atomic number 25 complexes had the power to catalyze the crooked epoxidation of unfunctionalized olefins, providing enantiomeric excesses that regularly reaching 90% and sometimes exceeding 98% . The chiral manganese complex Jacobsen apply was [(R,R)-N,N-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato-(2-)]-manganese (III) chloride (Jacobsens Catalyst). (R,R) Jacobsens Catalyst Jacobsens catalyst opens up little(a) pathways to enantiomerically pure pharmacologic and industrial products via the synthetically versatile epoxy function .         In this paper, a implication of Jacobsens catalyst is achieveed (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 change byproduct.

        Jacobsens oeuvre is important because it presents twain a reagent and a method acting to selectively guide an enantiomeric catalytic reaction of industrial and pharmacological importance. very few reagents, permit alone methods, are cognize to be able to perform such a function, which indicates the in truth innovational importance of Jacobsens work. Experimental Section          ecumenical Protocol. 99% L-(+)- Tartaric Acid, ethanol, dihydronaphthalene and stock-still acetic acid were obtained from the Aldrich chemical substance Company. 1,2 diaminocyclohexane (98% mix of cis/trans isomers) and heptane were obtained from the Acros Chemical Company. dichloromethane and chiliad carbonate were obtained from the EM Science division of EM Industries, If you sine qua non to get a full essay, order it on our website: Orderessay

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