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

Fingerprint

Crown Ethers
Esters
Salts
Amino Acids
Crowns
Nuclear magnetic resonance
dithiol
Proton Magnetic Resonance Spectroscopy

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

@article{0682abf8d3764ca5a6cd18b5a373104d,
title = "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",
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.",
author = "Tatsuro Yasukata and Shigeki Sasak and Kenji Koga",
year = "1991",
month = "1",
day = "1",
doi = "10.1248/cpb.39.530",
language = "English",
volume = "39",
pages = "530--532",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "The Pharmaceutical Society of Japan",
number = "2",

}

TY - JOUR

T1 - 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

AU - Yasukata, Tatsuro

AU - Sasak, Shigeki

AU - Koga, Kenji

PY - 1991/1/1

Y1 - 1991/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0025974847&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025974847&partnerID=8YFLogxK

U2 - 10.1248/cpb.39.530

DO - 10.1248/cpb.39.530

M3 - Article

AN - SCOPUS:0025974847

VL - 39

SP - 530

EP - 532

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 2

ER -