Stereoelectronic basis for the kinetic resolution of N-heterocycles with chiral acylating reagents.
The kinetic resolution of N-heterocycles with chiral acylating agents reveals a previously unrecognized stereoelectronic effect in amine acylation. Combined with a new achiral hydroxamate, this effect makes possible the resolution of various N-heterocycles by using easily prepared reagents. A transition-state model to rationalize the stereochemical outcome of this kinetic resolution is also proposed.
Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 1-5, 8093 Zürich (Switzerland), Fax: (+41) 44-633-1235.
Sheng-Ying
SY
Hsieh
Benedikt
B
Wanner
Philip
P
Wheeler
André M
AM
Beauchemin
Tomislav
T
Rovis
Jeffrey W
JW
Bode
D000215:Acylation; D002384:Catalysis; D007700:Kinetics; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
N-heterocycles; hydroxamic acid; kinetic resolution; stereoelectronic effects; synthetic methods