170508-73-3Relevant academic research and scientific papers
A new procedure for the reduction of α,β-unsaturated pyrrolidinones to 2H-pyrroles and 1H-pyrroles based on initial activation by N-nitrosation
Spivey, Alan C.,Frampton, Christopher S.,Battersby, Alan R.
, p. 2103 - 2110 (1996)
A new two step procedure is developed for the half-reduction of lactams to cyclic imines and enamines. N-Nitrosation using dinitrogen tetroxide furnishes N-nitroso lactams, which undergo chemoselective 1,2-reduction to N-nitroso carbinolamines? by one equivalent of hydride delivered from lithium triethylborohydride. The nitroso group is cleaved in a novel way using samarium(II) iodide and dehydration then generates the corresponding imine (which may tautomerise to the isomeric enamine). The reduction can be performed in the presence of esters and has proved efficient for the preparation of 2H-pyrroles (pyrrolenines) and 1H-pyrroles relevant to the study of tetrapyrrole biosynthesis.
Stereochemical Studies on the Proposed Spiro Intermediate for the Biosynthesis of the Natural Porphyrins: Determination by a Novel X-Ray Method of the Absolute Configuration of the Spirolactam which Inhibits Cosynthetase
Spivey, Alan C.,Capretta, Alfredo,Frampton, Christopher S.,Leeper, Finian J.,Battersby, Alan R.
, p. 1789 - 1790 (1995)
A novel X-ray analysis, combined with correlations by circular dichroism, has been used to establish the (R)-configuration at the stereocentre in that enantiomer of the spirolactam 4 which strongly inhibits uroporphyrinogen III synthase.
