827624-06-6Relevant articles and documents
The elusive enamine intermediate in proline-catalyzed aldol reactions: NMR detection, formation pathway, and stabilization trends
Schmid, Markus B.,Zeitler, Kirsten,Gschwind, Ruth M.
supporting information; experimental part, p. 4997 - 5003 (2010/09/15)
The missing link: The elusive enamine intermediate of nucleophilic proline catalysis was detected and stereochemically characterized by NMR analysis of the aldehyde self-aldolization reaction in dipolar aprotic solvents. NMR exchange spectroscopy (EXSY) w
Behaviour of Aminoacids and Aliphatic Aldehydes in Dipolar Aprotic Solvents: Formation of Oxazolidinones
Orsini, F.,Pelizzoni, F.,Forte, M.,Sisti, M.,Bombieri, G.,Benetollo, F.
, p. 837 - 841 (2007/10/02)
Reactions of aliphatic branched aldehydes with proline in dimethyl sulfoxide or acetonitrile solution afford oxazolidin-5-ones with high diastereoselection.Linear aldehydes afford aldolic/crotonic condensation products; with short reaction times, the presence of oxazolidinones can be detected in the pmr spectra.Acyclic aminoacids and branched aldehydes yield a reaction mixture the pmr and ir spectra of which give evidence for iminic-oxazolidinone equilibria.The structure of (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclooctan-4-one has been confirmed by X-ray diffraction analysis.