Convenient synthesis of novel C2-symmetric bisoxazolidine derivatives containing a sulfonamide moiety

A new series of C₂-symmetric bisoxazolidines containing a sulfonamide moiety has been prepared. The synthesis started by reducing the bisaminoester sulfonamides derived from natural amino acids by lithium aluminum hydride (LiAlH₄). The bisaminoalcohol sulfonamides resulting from the reduction react with aliphatic and aromatic aldehydes in an acidic medium to form heterocyclic compounds. The obtained N,N’-sulfonyl-bisoxazolidines are isolated in good yields. Bisoxazolidines derived from paraformaldehyde crystallize in ether, yielding their bridged [4.4.1] bicyclic isomers. The structures of synthesized compounds have been explored and validated using standard spectroscopic techniques, such as NMR, IR, and mass spectrometry.