Behaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents: Formation of oxazolidinones—behaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents

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Abstract
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‐oxabiciclo‐[3.3.0]octan‐4‐one has been confirmed by X‐ray diffraction analysis.