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

Sang Hyeup Lee, Juyoung Yoon, Kensuke Nakamura, Yoon Sik Lee

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

cis- and trans-Oxazoline-5-carboxylates were synthesized effeciently 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 calculation, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio ester and anti diamino ester were synthesized from these cis- and trans- oxazoline-5-carboxylates.

Original languageEnglish
Pages (from-to)1243-1246
Number of pages4
JournalOrganic Letters
Volume2
Issue number9
DOIs
StatePublished - 4 May 2000

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