Cucurbituril: Chiral Applications

Anthony Day, Ashraf GHANEM

Research output: Contribution to journalReview article

21 Citations (Scopus)

Abstract

This review brings together the past and current methods for synthesizing the classical cucurbit[ n]uril (Q[n]), structural variants, and derivatives. Here we refer to the first family of Q[n] as "classical," where the cavity is spheroidal and carry no substituents at any of the equatorial methine carbons or the methylene bridging carbons. The synthetic background and general physical and chemical properties of the Q[n] as molecular hosts is discussed. Particular attention is drawn to the synthesis of structural variants that have signi ficance for chiral recognition properties such as (±)-bis-nor-seco-Q[6] and (±)-bis-nor-seco-Q[10]. Furthermore, examples of chiral recognition, enantio- and stereoselectivity using the achiral Q[n] as supramolecular structures with a chiral function directly or indirectly via another chiral agent are also

Original languageEnglish
Pages (from-to)712-723
Number of pages12
JournalChirality
Volume26
Issue number11
DOIs
Publication statusPublished - 2014

Fingerprint

Carbon
Stereoselectivity
Enantioselectivity
Chemical properties
Physical properties
Derivatives
cucurbituril
Bis-Q

Cite this

Day, Anthony ; GHANEM, Ashraf. / Cucurbituril: Chiral Applications. In: Chirality. 2014 ; Vol. 26, No. 11. pp. 712-723.
@article{0a4f2dd506a24398bc25bfb95e71e733,
title = "Cucurbituril: Chiral Applications",
abstract = "This review brings together the past and current methods for synthesizing the classical cucurbit[ n]uril (Q[n]), structural variants, and derivatives. Here we refer to the first family of Q[n] as {"}classical,{"} where the cavity is spheroidal and carry no substituents at any of the equatorial methine carbons or the methylene bridging carbons. The synthetic background and general physical and chemical properties of the Q[n] as molecular hosts is discussed. Particular attention is drawn to the synthesis of structural variants that have signi ficance for chiral recognition properties such as (±)-bis-nor-seco-Q[6] and (±)-bis-nor-seco-Q[10]. Furthermore, examples of chiral recognition, enantio- and stereoselectivity using the achiral Q[n] as supramolecular structures with a chiral function directly or indirectly via another chiral agent are also",
keywords = "cucurbituril, chiral-recognition, enantioselectivity, stereoselectivity, host–-guest-properties, supramolecular-chemistry",
author = "Anthony Day and Ashraf GHANEM",
year = "2014",
doi = "10.1002/chir.22363",
language = "English",
volume = "26",
pages = "712--723",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "11",

}

Cucurbituril: Chiral Applications. / Day, Anthony; GHANEM, Ashraf.

In: Chirality, Vol. 26, No. 11, 2014, p. 712-723.

Research output: Contribution to journalReview article

TY - JOUR

T1 - Cucurbituril: Chiral Applications

AU - Day, Anthony

AU - GHANEM, Ashraf

PY - 2014

Y1 - 2014

N2 - This review brings together the past and current methods for synthesizing the classical cucurbit[ n]uril (Q[n]), structural variants, and derivatives. Here we refer to the first family of Q[n] as "classical," where the cavity is spheroidal and carry no substituents at any of the equatorial methine carbons or the methylene bridging carbons. The synthetic background and general physical and chemical properties of the Q[n] as molecular hosts is discussed. Particular attention is drawn to the synthesis of structural variants that have signi ficance for chiral recognition properties such as (±)-bis-nor-seco-Q[6] and (±)-bis-nor-seco-Q[10]. Furthermore, examples of chiral recognition, enantio- and stereoselectivity using the achiral Q[n] as supramolecular structures with a chiral function directly or indirectly via another chiral agent are also

AB - This review brings together the past and current methods for synthesizing the classical cucurbit[ n]uril (Q[n]), structural variants, and derivatives. Here we refer to the first family of Q[n] as "classical," where the cavity is spheroidal and carry no substituents at any of the equatorial methine carbons or the methylene bridging carbons. The synthetic background and general physical and chemical properties of the Q[n] as molecular hosts is discussed. Particular attention is drawn to the synthesis of structural variants that have signi ficance for chiral recognition properties such as (±)-bis-nor-seco-Q[6] and (±)-bis-nor-seco-Q[10]. Furthermore, examples of chiral recognition, enantio- and stereoselectivity using the achiral Q[n] as supramolecular structures with a chiral function directly or indirectly via another chiral agent are also

KW - cucurbituril

KW - chiral-recognition

KW - enantioselectivity

KW - stereoselectivity

KW - host–-guest-properties

KW - supramolecular-chemistry

UR - http://www.scopus.com/inward/record.url?scp=84910022393&partnerID=8YFLogxK

U2 - 10.1002/chir.22363

DO - 10.1002/chir.22363

M3 - Review article

VL - 26

SP - 712

EP - 723

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 11

ER -