Synthesis and optical resolution of naphthalene-containing inherently chiral calix[4]arenes derived by intramolecular ring closure or stapling of proximal phenyl units

Atsushi Ikeda, Makoto Yoshimura, Pavel Lhotak, Seiji Shinkai

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

New methods for the preparation of inherently chiral calix[4]arenes have been developed. The molecular asymmetry in these calix[4]arenes is created by an asymmetrical disposition of naphthalene rings on the upper rim. In compound 1, monoformylcalix[4]arene 5 was transformed into naphthalene-containing calix[4]arene by ring closure. In compound 2, p-chloromethyl groups are intramolecularly cross-linked with 3-hydroxymethyl-2-naphthol. This 'stapling reaction' results in a syn isomer 2a and an anti isomer 2b, the latter being classified into an inherently chiral calix[4]arene. Racemic anti 2 could be 'perfectly' optically resolved by an HPLC method with a chiral-packed column. The chiral products were thoroughly characterized by various spectroscopic methods. These results indicate that the naphthalene skeleton is very useful for creating molecular asymmetry in calix[4]arenes.

Original languageEnglish
Pages (from-to)1945-1950
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number16
DOIs
Publication statusPublished - Aug 21 1996

Fingerprint

Isomers
naphthalene
calix(4)arene
2-naphthol

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Synthesis and optical resolution of naphthalene-containing inherently chiral calix[4]arenes derived by intramolecular ring closure or stapling of proximal phenyl units. / Ikeda, Atsushi; Yoshimura, Makoto; Lhotak, Pavel; Shinkai, Seiji.

In: Journal of the Chemical Society - Perkin Transactions 1, No. 16, 21.08.1996, p. 1945-1950.

Research output: Contribution to journalArticle

@article{495d431612c64938ae1afcd552477e0d,
title = "Synthesis and optical resolution of naphthalene-containing inherently chiral calix[4]arenes derived by intramolecular ring closure or stapling of proximal phenyl units",
abstract = "New methods for the preparation of inherently chiral calix[4]arenes have been developed. The molecular asymmetry in these calix[4]arenes is created by an asymmetrical disposition of naphthalene rings on the upper rim. In compound 1, monoformylcalix[4]arene 5 was transformed into naphthalene-containing calix[4]arene by ring closure. In compound 2, p-chloromethyl groups are intramolecularly cross-linked with 3-hydroxymethyl-2-naphthol. This 'stapling reaction' results in a syn isomer 2a and an anti isomer 2b, the latter being classified into an inherently chiral calix[4]arene. Racemic anti 2 could be 'perfectly' optically resolved by an HPLC method with a chiral-packed column. The chiral products were thoroughly characterized by various spectroscopic methods. These results indicate that the naphthalene skeleton is very useful for creating molecular asymmetry in calix[4]arenes.",
author = "Atsushi Ikeda and Makoto Yoshimura and Pavel Lhotak and Seiji Shinkai",
year = "1996",
month = "8",
day = "21",
doi = "10.1039/p19960001945",
language = "English",
pages = "1945--1950",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "1472-7781",
publisher = "Chemical Society",
number = "16",

}

TY - JOUR

T1 - Synthesis and optical resolution of naphthalene-containing inherently chiral calix[4]arenes derived by intramolecular ring closure or stapling of proximal phenyl units

AU - Ikeda, Atsushi

AU - Yoshimura, Makoto

AU - Lhotak, Pavel

AU - Shinkai, Seiji

PY - 1996/8/21

Y1 - 1996/8/21

N2 - New methods for the preparation of inherently chiral calix[4]arenes have been developed. The molecular asymmetry in these calix[4]arenes is created by an asymmetrical disposition of naphthalene rings on the upper rim. In compound 1, monoformylcalix[4]arene 5 was transformed into naphthalene-containing calix[4]arene by ring closure. In compound 2, p-chloromethyl groups are intramolecularly cross-linked with 3-hydroxymethyl-2-naphthol. This 'stapling reaction' results in a syn isomer 2a and an anti isomer 2b, the latter being classified into an inherently chiral calix[4]arene. Racemic anti 2 could be 'perfectly' optically resolved by an HPLC method with a chiral-packed column. The chiral products were thoroughly characterized by various spectroscopic methods. These results indicate that the naphthalene skeleton is very useful for creating molecular asymmetry in calix[4]arenes.

AB - New methods for the preparation of inherently chiral calix[4]arenes have been developed. The molecular asymmetry in these calix[4]arenes is created by an asymmetrical disposition of naphthalene rings on the upper rim. In compound 1, monoformylcalix[4]arene 5 was transformed into naphthalene-containing calix[4]arene by ring closure. In compound 2, p-chloromethyl groups are intramolecularly cross-linked with 3-hydroxymethyl-2-naphthol. This 'stapling reaction' results in a syn isomer 2a and an anti isomer 2b, the latter being classified into an inherently chiral calix[4]arene. Racemic anti 2 could be 'perfectly' optically resolved by an HPLC method with a chiral-packed column. The chiral products were thoroughly characterized by various spectroscopic methods. These results indicate that the naphthalene skeleton is very useful for creating molecular asymmetry in calix[4]arenes.

UR - http://www.scopus.com/inward/record.url?scp=33748905328&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748905328&partnerID=8YFLogxK

U2 - 10.1039/p19960001945

DO - 10.1039/p19960001945

M3 - Article

AN - SCOPUS:33748905328

SP - 1945

EP - 1950

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 1472-7781

IS - 16

ER -