trans-1,2-Diaminocyclohexane is an organic compound with the formula C6H10(NH2)2. This diamine is a building block for C2-symmetric ligands that are useful in asymmetric catalysis.[1]
A mixture of all three stereoisomers of 1,2-diaminocyclohexane is produced by the hydrogenation of o-phenylenediamine. It is also side product in hydrogenation of adiponitrile. The racemic trans isomer (1:1 mixture of (1R,2R)-1,2-diaminocyclohexane and (1S,2S)-1,2-diaminocyclohexane) can be separated into the two enantiomers using enantiomerically pure tartaric acid as the resolving agent.[2]
Derived ligands
Representative ligands prepared from (1R,2R)- or (1S,2S)-1,2-diaminocyclohexane are diaminocyclohexanetetraacetic acid (CyDTAH4), Trost ligand, and the salen analogue used in the Jacobsen epoxidation.
References
- ^ Kouklovsky, Cyrille; Langlois, Yves (2003). "(1S,2S)-1,2-Diaminocyclohexane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00145. ISBN 0471936235.
- ^ Jay F. Larrow and Eric N. Jacobsen (2004). "(R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst". Organic Syntheses; Collected Volumes, vol. 10, p. 96.
