Asymmetric Epoxidation Of Dihydronaphthalene With A Synthesized Jacobsen's Catalyst

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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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8 cm-1, 16 scans standard method, 500cm-1 - 4000cm-1). Flash
Chromatography was carried out in a 20 mm column with an eluant of ethyl acetate
(25%) in hexane.

(R,R)-1,2 Diaminocyclohexane mono-(+)-tartrate salt. 99% L-(+)-Tartaric
Acid (7.53g, 0.051mol) was added in one portion to a 150 mL beaker equipped
with distilled H2O (25 mL) magnetic stir bar, and thermometer. Once the
temperature had dropped to 17.8 °C, 1,2 diaminocyclohexane (11.89 g, 12.5 mL,
0.104 mol) was added with stirring in one portion. To the resultant amber
solution was added glacial acetic acid (5.0 mL, 0.057 mol). The frothy orange
product was cooled in an ice water bath for 30 minutes. The product was ...

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