498542-97-5Relevant articles and documents
Tuning the enantioselective N-acetylation of racemic amines: A spectacular salt effect
Arseniyadis, Stellios,Subhash, Pithani V.,Valleix, Alain,Mathew, Suju P.,Blackmond, Donna G.,Wagner, Alain,Mioskowski, Charles
, p. 6138 - 6139 (2005)
We have described a spectacular salt effect in the kinetic resolution of (±)-1-phenylethylamine, which leads to an increase in reactivity, high levels of selectivity, and a complete reversal of the stereoselectivity. By tuning the reaction conditions, we
Kinetic resolution of amines: A highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity
Arseniyadis, Stellios,Valleix, Alain,Wagner, Alain,Mioskowski, Charles
, p. 3314 - 3317 (2007/10/03)
Solvents lend a hand: Changing the polarity of the reaction solvent from 1,3-dimethyltetrahydropyrimidin-2-one (DMPU) to toluene reverses the stereo-selectivity observed in the acetylation of amines with (1S,2S)-1 (see scheme). Optimizing the reaction conditions led to an unprecedented 90% ee (S) in DMPU at -20°C with a 33% conversion.