Novel bicyclic chiral crown ethers having a p-xylenedioxy unit with improved complex stability and rate-enhancement in the intra-complex thiolysis of α-amino acid ester salts

Tatsuro Yasukata, Shigeki Sasak, Kenji Koga

Research output: Contribution to journalArticle

Abstract

Novel bicyclic chiral crown ethers having an a, al-p-xylenedioxy unit were synthesized. Crown dithiol 1 with a p-xylenedioxy bridge-structure performed intra-complex thiolysis with a-amino acid p-nitrophenyl ester HBr salts much faster than the corresponding dithiol 3 without the bridge-structure. A 1H-NMR study suggested that the increased rate of intra-complex thiolysis is due to increased stability of the intermediary complex during the reaction.

Original languageEnglish
Pages (from-to)530-532
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume39
Issue number2
DOIs
Publication statusPublished - Jan 1 1991
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

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