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 payoff (R,R)-1,2-diaminocyclohexane mono-(+)-tartrate salt. The tartrate salt was then reacted with lovemaking oil carbonate and 3,5-di-tert-butylsalicylaldehyde to stand (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 throttle. The synthesized Jacobsens gas pedal was use to catalyze the epoxidation of dihydronaphthalene. The products of this answer were isolated, and it was found that the product yielded 1,2- pastedihydronaphthalene as soundly as naphthalene. Introduction         In 1990, professor E.N. Jacobsen reported that chiral atomic number 25 complexes had the power to catalyze the lopsided epoxidation of unfunctionalized alkenes, providing enantiomeric excesses that regularly reaching 90% and sometimes exceeding 98% . The chiral manganese complex Jacobsen employ 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 soon pathways to enantiomerically pure pharmacologic and industrial products via the synthetically versatile epoxy function .         In this paper, a implication of Jacobsens catalyst is bring to passed (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 some(prenominal) a reagent and a rule to selectively guide an enantiomeric catalytic reaction of industrial and pharmacological importance. very few reagents, let alone methods, are know to be able to perform such a function, which indicates the genuinely innovational importance of Jacobsens work. Experimental Section          worldwide Protocol. 99% L-(+)- Tartaric Acid, ethanol, dihydronaphthalene and rimed acetic acid were obtained from the Aldrich chemic 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: Ordercustompaper.com

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