Asymmetric Epoxidation Of Dihydronaphthalene With A Synthesized Jacobsen's Catalyst


Asymmetric Epoxidation of Dihydronaphthalene with a Synthesized Jacobsen's
Chem 250 GG
Abstract. 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 ...

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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 Section

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 ...

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"Asymmetric Epoxidation Of Dihydronaphthalene With A Synthesized Jacobsen's Catalyst." Essayworld.com. March 30, 2006. Accessed May 23, 2015. http://www.essayworld.com/essays/Asymmetric-Epoxidation-Dihydronaphthalene-Synthesized-Jacobsens-Catalyst/43578.
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Added: 3/30/2006 08:17:12 AM
Category: Science & Nature
Words: 2135
Pages: 8

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