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DOI: 10.1055/s-0033-1339302
(1R,2R)-Diaminocyclohexane
Publikationsverlauf
Publikationsdatum:
26. Juni 2013 (online)
Introduction
trans-1,2-Diaminocyclohexane (1), denoted as trans-DACH, is a chiral molecule with C 2 symmetry. It was synthesized for the first time in 1926 from hexahydrophthalic acid by Wieland.[1] A convenient way for the resolution of the enantiomers was introduced by Whitney in 1980.[2] An aqueous solution of racemic trans-DACH and enantiomerically pure l-(–)-tartaric acid was treated with glacial acetic acid and the resulting white precipitate of enantiomerically pure (1R,2R)-diaminocyclohexane tartarate was subsequently treated with an aqueous solution of KOH yielding 1 (Scheme [1]). Recently, it was demonstrated that the second enantiomer can be recovered from the resulting filtrate with another portion of l-(–)-tartaric acid.[3]
In the early 1990s, Jacobsen and co-workers published two subsequent papers on the enantioselective oxidation of olefins catalyzed by an imine complex derived from (1R,2R)-diaminocyclohexane.[4] Since then, the interest in DACH-based compounds in chiral synthesis has been growing. Although many derivatives of the compound have been applied in chiral catalysis, recent years brought catalytic and synthetic applications of trans-DACH itself.
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References and Notes
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