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 pungent to yield (R,R)-1,2-diaminocyclohexane mono-(+)-tartrate salt. The tartrate salt was thus reacted with honey oil 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 design Jacobsens catalyst. The synthesized Jacobsens catalyst was use 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 soundly as naphthalene. Introduction         In 1990, professor E.N. Jacobsen account that chiral manganese labyrinthianes had the power to catalyze the asymmetric epoxidation of un formalized alkenes, providing enantiomeric excesses that regularly stretching 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 (Jacobsens Catalyst). (R,R) Jacobsens Catalyst Jacobsens catalyst opens up short pathways to enantiomerically exquisite pharmacological and industrial products via the synthetically versatile epoxy function .         In this paper, a implication of Jacobsens 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 rise as an oxidized byproduct.

        Jacobsens oeuvre 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 unaccompanied methods, are known to be able to perform such(prenominal) a function, which indicates the truly innovational importance of Jacobsens work. Experimental piece         General 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 chiliad carbonate were obtained from the EM Science division of EM Industries, If you sine qua non to come a full essay, order it on our website: OrderCustomPaper.com

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