Lithiation-electrophilic trapping of N-sulfonyl-activated ethylene aziridines.
A detailed study on the lithiation-electrophilic trapping of N-sulfonyl ethylene aziridines is described. The optimum results required use of a N-2,4,6-tri-iso-propylbenzenesulfonyl activating group and lithiation using 3 equiv. of s-BuLi-PMDETA for 1 minute before addition of the electrophile. In situ trapping with Me3SiCl was also successful. Electrophilic trapping with aldehydes provided a stereoselective route to syn-hydroxy aziridines. Alternatively, keto aziridines could be stereoselectively reduced to syn-hydroxy aziridines using NaBH4-CeCl3. The relative stereochemistry in two of the hydroxy aziridines was established unequivocally by X-ray crystallography.
Huang
Jianhui
J
Department of Chemistry, University of York, Heslington, York, UK.
Moore
Stephen P
SP
O'Brien
Peter
P
Whitwood
Adrian C
AC
Gilday
John
J
D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D005030:Ethylenes / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D013237:Stereoisomerism
D001388:Aziridines; D005030:Ethylenes; C036216:ethylene; D008094:Lithium