The chemistry, synthetic routes and medicinal properties of vicinal diamines and imidazolines are discussed. Synthetic routes towards chemically and pharmaceutically important molecules containing vicinal diamine functionality are discussed in detail. This mini review article covers the new developments of diamine chemistry between 2000 and 2005.

This microreview presents the development of the catalytic aminohalogenation of olefins. The olefin substrates include electron‐deficient and functionalized ones, such as α,β‐unsaturated esters, α,β‐unsaturated ketones and α,β‐unsaturated nitriles. In addition, the first asymmetric aminohalogenation by the use of Evans chiral auxiliaries is also discussed. The convincing evidence is provided to support the aziridinium mechanism of aminohalogenation reaction. The applications of this reaction are described by converting vicinal haloamines into other important synthetic building blocks. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

The chemical shifts of the aromatic hydrogens of 12 symmetrical imidazolium salts were determined in different deuterated solvents. Based on the magnitude of the chemical shift change for the hydrogens of the imidazolium ion in the various solvents, relationships were developed to determine the relative solute/solvent interactions for these compounds. Owing to different degrees of interactions involving the aromatic hydrogens of the imidazolium cations and anions, there is a variation in the interaction of the hydrogens with the solvent molecules. The intimate interaction that exists between the hydrogens of the imidazolium cation and the BF anion results in the BF salts being less solvated compared with salts containing BF and SbF anions. For imidazolium salts that contain C2H5, C4H9 and C8H17 side‐chains bonded in the 1 and 3 positions, the interaction between H2 and the solvents was observed to be greater than for imidazolium salts with C16H33 substituents. On the other hand, for imidazolium salts that have C16H33 substituents the interaction between H2 and the solvents is similar to that for H4 and H5. Copyright © 2005 John Wiley & Sons, Ltd.

[reaction: see text] The first asymmetric aminohalogenation of functionalized alkenes has been established. The ionic liquid [bmim][BF4] was found to be the only effective media for success as normal organic solvents failed to give any product for this reaction. The reaction is also very convenient to perform by simply mixing the three reactants, cinnamates, N,N-dichloro-p-toluenesulfonamide, and catalyst, together with 4 A molecular sieves at room temperature in [bmim][BF4] in any convenient vial of appropriate size without special protection from inert gases. Good chemical yields (60-72%) and diastereoselectivities (up to 75% de) have been obtained with a good scope of substrates. The resulting individual diastereomers have been cleanly separated via column chromatography. The absolute stereochemistry of the reaction was unambiguously determined by X-ray structural analysis.