Chiral cage molecules generated by regioselective O-alkylation of a doubly-bridged calix[8]arene

Atsushi Ikeda, Yoshio Suzuki, Seiji Shinkai

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A calix[8]arene doubly-bridged at the 1,5-phenol units and 3,7-phenol units has a cage structure with D(2d) symmetry. Regioselective introduction of methyl groups into the residual 2,4,6,8-phenol units affords five different cage compounds: that is, three racemic compounds, one meso compound, and one achiral compound. This paper reports systematic studies on the preparation methods of these new cage compounds and spectroscopic classification of their molecular symmetries. The results indicate that these compounds have a latent potential as a platform for designing chiral cage molecules with an ionophoric inner cavity.

Original languageEnglish
Pages (from-to)97-105
Number of pages9
JournalTetrahedron Asymmetry
Volume9
Issue number1
DOIs
Publication statusPublished - Jan 16 1998

Fingerprint

alkylation
Alkylation
Phenol
phenols
Phenols
Molecules
molecules
symmetry
platforms
preparation
cavities

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Chiral cage molecules generated by regioselective O-alkylation of a doubly-bridged calix[8]arene. / Ikeda, Atsushi; Suzuki, Yoshio; Shinkai, Seiji.

In: Tetrahedron Asymmetry, Vol. 9, No. 1, 16.01.1998, p. 97-105.

Research output: Contribution to journalArticle

Ikeda, Atsushi ; Suzuki, Yoshio ; Shinkai, Seiji. / Chiral cage molecules generated by regioselective O-alkylation of a doubly-bridged calix[8]arene. In: Tetrahedron Asymmetry. 1998 ; Vol. 9, No. 1. pp. 97-105.
@article{8cc3aaad13884deda0da187dec7f34b0,
title = "Chiral cage molecules generated by regioselective O-alkylation of a doubly-bridged calix[8]arene",
abstract = "A calix[8]arene doubly-bridged at the 1,5-phenol units and 3,7-phenol units has a cage structure with D(2d) symmetry. Regioselective introduction of methyl groups into the residual 2,4,6,8-phenol units affords five different cage compounds: that is, three racemic compounds, one meso compound, and one achiral compound. This paper reports systematic studies on the preparation methods of these new cage compounds and spectroscopic classification of their molecular symmetries. The results indicate that these compounds have a latent potential as a platform for designing chiral cage molecules with an ionophoric inner cavity.",
author = "Atsushi Ikeda and Yoshio Suzuki and Seiji Shinkai",
year = "1998",
month = "1",
day = "16",
doi = "10.1016/S0957-4166(97)00611-3",
language = "English",
volume = "9",
pages = "97--105",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "1",

}

TY - JOUR

T1 - Chiral cage molecules generated by regioselective O-alkylation of a doubly-bridged calix[8]arene

AU - Ikeda, Atsushi

AU - Suzuki, Yoshio

AU - Shinkai, Seiji

PY - 1998/1/16

Y1 - 1998/1/16

N2 - A calix[8]arene doubly-bridged at the 1,5-phenol units and 3,7-phenol units has a cage structure with D(2d) symmetry. Regioselective introduction of methyl groups into the residual 2,4,6,8-phenol units affords five different cage compounds: that is, three racemic compounds, one meso compound, and one achiral compound. This paper reports systematic studies on the preparation methods of these new cage compounds and spectroscopic classification of their molecular symmetries. The results indicate that these compounds have a latent potential as a platform for designing chiral cage molecules with an ionophoric inner cavity.

AB - A calix[8]arene doubly-bridged at the 1,5-phenol units and 3,7-phenol units has a cage structure with D(2d) symmetry. Regioselective introduction of methyl groups into the residual 2,4,6,8-phenol units affords five different cage compounds: that is, three racemic compounds, one meso compound, and one achiral compound. This paper reports systematic studies on the preparation methods of these new cage compounds and spectroscopic classification of their molecular symmetries. The results indicate that these compounds have a latent potential as a platform for designing chiral cage molecules with an ionophoric inner cavity.

UR - http://www.scopus.com/inward/record.url?scp=0032536010&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032536010&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(97)00611-3

DO - 10.1016/S0957-4166(97)00611-3

M3 - Article

AN - SCOPUS:0032536010

VL - 9

SP - 97

EP - 105

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 1

ER -