Tuning the enantioselective N-acetylation of racemic amines: a spectacular salt effect.
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 were able to increase the selectivity factor of (1S,2S)-1 to s = 115.
Arseniyadis
Stellios
S
Laboratoire de Synthèse Bio-Organique associé au CNRS, Université Louis Pasteur de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch-Graffenstaden, France.
Subhash
Pithani V
PV
Valleix
Alain
A
Mathew
Suju P
SP
Blackmond
Donna G
DG
Wagner
Alain
A
Mioskowski
Charles
C