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Trans-1,2-diaminocykloheksan – niezwykła kariera outsidera

Petryk M., Kwit M.

Wiadomości Chemiczne

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2013

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[Z] 67, 5-6

393--442

EN

An enantiopure trans-1,2-diaminocyclohexane is one of the most widely used chiral diamines in modern organic chemistry. This chiral building block, readily available from waste industrial products, emerges as a major figure in the field of asymmetric synthesis. The unique structural and conformational properties of trans-1,2-diaminocyclohexane make it very useful for the development of new synthetic strategies, taking advantage of its geometrical pre-organization. In this short article, we will highlight the utility of enantiomerically pure trans-1,2-diaminocyclohexane derivatives as broad-range chiral reagents and ligands for catalytic cycles. A brief overview of the aspects of applications in the field of molecular recognition will also be given.

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Eksperymentalne i teoretyczne oznaczanie konfiguracji absolutnej związków chiralnych metodami chiralooptycznymi

Kwit M.

Wiadomości Chemiczne

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2011

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[Z] 65, 1-2

33-58

EN

Chirality is of paramount importance in chemistry and life sciences. Electronic circular dichroism (ECD) as well as optical rotation (OR) are fundamental properties of chiral molecules. These chiroptical properties provide rich information about conformation and configuration of the molecules. Although empirical correlations between chiroptical phenomena, mostly ECD, and molecular stereochemistry have existed for some time, the development of new accurate theoretical methods opened new opportunities for correlation of chiroptical properties with structure. Computational chemistry has made an amazing progress during the past two decades, moving this highly specialized discipline into the mainstream, and making a renaissance in chiroptical methods. This short review is meant as an introduction to the modern approach to optical activity of chiral molecules. Some illustrative applications will put the emphasis on practical applications of the theoretical/experimental analysis of complex molecules including highly flexible bistramide C and noncovalently bonded donor-acceptor dyad. The importance of the solvent effect is briefly discussed and a typical methodology is described and its strengths and weak points are commented.

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Synthesis and Structure of N,N'-Diaryl Derivatives of trans-1,2-Diaminocyclohexane

Kwit M., Kubicki M., Borowiak T., Gawroński J.

Polish Journal of Chemistry

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2003

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Vol. 77 / nr 11

1669-1682

EN

Synthesis of N,N_-diaryl derivatives of trans-1,2-diaminocyclohexane (DACH) by palladium- catalyzed aromatic nucleophilic substitution reactions is described. The conformation of the N-acetylated N,N_-diaryl derivatives of DACH has been studied by the computational, circular dichroism and X-ray diffraction methods. Reversal of the relative orientation of the N-aryl residues due to N-acetylation has been established.