Synthesis of thiazol-2-imines from the reduction of single enantiomer 2-imino-thiazolidin-4-ones followed by a spontaneous water elimination.

Chiral hemiaminals (5-8RR and 5-8SS) have been synthesized from the corresponding 2-iminothiazolidine-4-ones (1-4RR and 1-4SS) by LiAlH4 reductions stereoselectively and were then converted to single enantiomer thiazol-2-imines (9-12RR and 9-12SS) by a water elimination reaction. The kinetics of the dehydration reactions which occurred spontaneously both in the solid state and in the solution have been followed by time dependent 1 H nuclear magnetic resonance spectroscopy. The corresponding first order rate constants and free energies of activation values for the conversions have been reported.