124770-20-3Relevant academic research and scientific papers
Synthesis of Chiral Cyclic α-p-Tolylsulphinyl Ketones
Carreno, M. Carmen,Ruano, Jose L. Garcia,Pedregal, Concepcion,Rubio, Almudena
, p. 1335 - 1337 (2007/10/02)
Two new syntheses of optically pure cyclic β-oxo sulphoxides are described.Reactions of (-)-menthyl toluene-p-sulphinate with cycloalkanones (CH2)nCO (n = 4, 5, and 6) and iPr2NMgBr yield mixtures of diastereoisomeric sulphoxides without epimerization at sulphur.With the cyclopentanone (n = 4) yields are poor owing to competitive autocondensation of the ketone.Reactions of cycloalkanone N-phenylimines with the sulphinate in the presence of lithium di-isopropylamide afford, after chromatographic purification, the same mixtures of diastereoisomeric β-oxo sulphoxides with no aldolic condensation product.
