113317-83-2Relevant academic research and scientific papers
Regioselectivity in Lateral Deprotonation of an Isoxazolecarboxamide of (S)-Prolinol. Conformational Correlation by Crystal Structure, Solid State and Solution 13C NMR
Schlicksupp, Ludwig,Natale, N. R.
, p. 1345 - 1348 (2007/10/02)
The conformation at the amide functional group in 3,5-dimethylisoxazole-4-(S-2'-hydroxymethyl-N-pyrrolidino)carboxamide (1) has been determined by a single crystal X-ray determination.The 13C nmr in both deuteriochloroform solution and solid state show close agreement.The metalation behaviour of the amide is dependent upon the substitution on the 2'-hydroxymethyl moiety.Dianion studies indicate C-5 lateral metalation under both thermodynamic and kinetic conditions.Protection of this substituent as the methyl ether, 2, gives rise to predominant C-3 lateral metalation under kinetic conditions and C-5 lateral metalation on equilibration.These observations can be explained using the Ireland-Evans model for chelation directed deprotonation.
