Ever since Nugent first reported a practical, catalytic method for the enantioselective opening of meso-epoxides with trimethylsilyl azide (TMSN3), [1] such desymmetrization reactions of epoxides and aziridines using a variety of nucleophiles have been the subject of extensive research. The less developed ring-opening reactions, those of meso-aziridines by carbon and nitrogen nucleophiles, give...

The ring-opening of epoxides with potassium trifluoroborates proceeds smoothly in the presence of trifluoroacetic anhydride under metal-free conditions. The reactions are regioselective and afford a single diastereomer. Both electron-rich and electron-poor aryltrifluoroborates are tolerated.

Halohydrin dehalogenases catalyse the conversion of vicinal halohydrins into their corresponding epoxides, while releasing halide ions. They can be found in several bacteria that use halogenated alcohols or compounds that are degraded via halohydrins as a carbon source for growth. Biochemical and structural studies have shown that halohydrin dehalogenases are evolutionarily and mechanistically ...

Highly fluorinated epoxides were polymerized under mild conditions regioregularly, which gave easy access to isotactic polymers by using optically pure epoxides.

A rational approach towards the borylative ring-opening of vinylepoxides and vinylaziridines, by the in situ formed MeO(-)→bis(pinacolato)diboron adduct, has been developed. The enhanced nucleophilic character of the Bpin (sp(2)) moiety from the reagent favours the SN2' conjugated B addition with the concomitant opening of the epoxide and aziridine rings. The reaction proceeds with total chemos...