Efficient syntheses and ring-opening reactions of trans- and cis-oxazoline-5-carboxylates

[formula: see text] cis- and trans-Oxazoline-5-carboxylates were synthesized efficiently from isopropyl trans-cinnamate utilizing the Sharpless AA reaction. trans-Oxazoline was much more reactive than the cis-isomer toward ring opening reactions. From ab initio molecular calculations, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio esters and anti diamino esters were synthesized from these cis- and trans-oxazoline-5-carboxylates.