Synlett 2013; 24(12): 1597-1598
DOI: 10.1055/s-0033-1339302
© Georg Thieme Verlag Stuttgart · New York


Paweł Tokarz
University of Łódź, Department of Organic Chemistry, Tamka 12, 91-403 Łódź, Poland   Email:
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Further Information

Publication History

Publication Date:
26 June 2013 (online)


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.

Zoom Image
Scheme 1
  • References and Notes

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    • 2a Whitney TA. U.S. Patent 4 085138, 1978
    • 2b Whitney TA. J. Org. Chem. 1980; 45: 4214
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    • 4b Jacobsen EN, Zhang W, Muci AR, Ecker JR, Deng L. J. Am. Chem. Soc. 1991; 113: 7063
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