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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)… Click to show full abstract
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.
Journal Title: Chirality
Year Published: 2020
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