Search

The zinc-induced reductive elimination from 5-deoxy-5-iodo derivatives of D-xylose and L-arabinose is carried out in order to study the structural parameters and the presence of [Zn.sup.2+] ions. The complexes between zinc and [Zn.sup.2+] bound carbohydrates are characterized with large stabilization energies, indicating that [Zn.sup.2+] might increase the affinity of the organic compound with the zinc metal surface.

A simple method was developed for the direct formation of unsaturated iminosugars starting from readily available [omega]-methanesulfonylglycononitriles. The nucleophilic addition/cyclization reaction with variation of the Grignard reagent allows for a range of different side chains to be incorporated to generate libraries of broussonetine analogues.

The scope and limitation of highly diastereoselective nucleophilic mono(trifluoromethylation) of a tartaric acid-based diketone reaction was studied by using trifluoromethyl(trimethyl)silane. The process was found to be an interesting way to convert one natural chiral raw material into two functionalized enantiopure building blocks including a trifluoromethyl one.

An unprecedented reactivity of CF3-TMS has been revealed, which exploits the basic character of the generated [CF3(-)] capable of delivering dichloromethide from dichloromethane with subsequent transfer to nitrones under smooth conditions. The proton-abstraction pathway was demonstrated through isotopic labeling experiments in CD2Cl2. The same reaction was achieved in acetonitrile with the introduction of a cyanomethyl group onto the nitrones.