Synthesis and properties of chiral molecular clefts related to Tröger's base

Jennifer J. Turner; Margaret M. Harding

doi:10.1080/10610270500073796

Synthesis and properties of chiral molecular clefts related to Tröger's base

Jennifer J. Turner, Margaret M. Harding^*

^*Corresponding author for this work

Research output: Contribution to journal › Review article › peer-review

18 Citations (Scopus)

Abstract

The chiral cavities present in 2,3:6,7-dibenzo-9-oxabicyclonona-2,6-diene, dibenzobicyclo[b,f][3.3.1]nona-5a, 6a-diene-6,12-dione, bicyclo[3.3.1]nonane and dibenzobicyclo[b,f][1,5]diazocines are reminiscent of Tröger's base, which has been widely used as a molecular cleft in supramolecular chemistry. The synthetic methodology to provide key derivatives for elaboration into new supramolecular structures, efficient resolution methods, the introduction of additional recognition groups and applications in supramolecular chemistry of these structurally related molecular clefts are reviewed.

Original language	English
Pages (from-to)	369-375
Number of pages	7
Journal	Supramolecular Chemistry
Volume	17
Issue number	5
DOIs	https://doi.org/10.1080/10610270500073796
Publication status	Published - Jul 2005
Externally published	Yes

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title = "Synthesis and properties of chiral molecular clefts related to Tr{\"o}ger's base",

abstract = "The chiral cavities present in 2,3:6,7-dibenzo-9-oxabicyclonona-2,6-diene, dibenzobicyclo[b,f][3.3.1]nona-5a, 6a-diene-6,12-dione, bicyclo[3.3.1]nonane and dibenzobicyclo[b,f][1,5]diazocines are reminiscent of Tr{\"o}ger's base, which has been widely used as a molecular cleft in supramolecular chemistry. The synthetic methodology to provide key derivatives for elaboration into new supramolecular structures, efficient resolution methods, the introduction of additional recognition groups and applications in supramolecular chemistry of these structurally related molecular clefts are reviewed.",

keywords = "Host-guest, Kagan's ether, Molecular cleft, Molecular recognition, Tr{\"o}ger's base, Tweezer",

author = "Turner, \{Jennifer J.\} and Harding, \{Margaret M.\}",

year = "2005",

month = jul,

doi = "10.1080/10610270500073796",

language = "English",

volume = "17",

pages = "369--375",

journal = "Supramolecular Chemistry",

issn = "1061-0278",

publisher = "Taylor and Francis Ltd.",

number = "5",

}

TY - JOUR

T1 - Synthesis and properties of chiral molecular clefts related to Tröger's base

AU - Turner, Jennifer J.

AU - Harding, Margaret M.

PY - 2005/7

Y1 - 2005/7

N2 - The chiral cavities present in 2,3:6,7-dibenzo-9-oxabicyclonona-2,6-diene, dibenzobicyclo[b,f][3.3.1]nona-5a, 6a-diene-6,12-dione, bicyclo[3.3.1]nonane and dibenzobicyclo[b,f][1,5]diazocines are reminiscent of Tröger's base, which has been widely used as a molecular cleft in supramolecular chemistry. The synthetic methodology to provide key derivatives for elaboration into new supramolecular structures, efficient resolution methods, the introduction of additional recognition groups and applications in supramolecular chemistry of these structurally related molecular clefts are reviewed.

AB - The chiral cavities present in 2,3:6,7-dibenzo-9-oxabicyclonona-2,6-diene, dibenzobicyclo[b,f][3.3.1]nona-5a, 6a-diene-6,12-dione, bicyclo[3.3.1]nonane and dibenzobicyclo[b,f][1,5]diazocines are reminiscent of Tröger's base, which has been widely used as a molecular cleft in supramolecular chemistry. The synthetic methodology to provide key derivatives for elaboration into new supramolecular structures, efficient resolution methods, the introduction of additional recognition groups and applications in supramolecular chemistry of these structurally related molecular clefts are reviewed.

KW - Host-guest

KW - Kagan's ether

KW - Molecular cleft

KW - Molecular recognition

KW - Tröger's base

KW - Tweezer

UR - https://www.scopus.com/pages/publications/23344434528

U2 - 10.1080/10610270500073796

DO - 10.1080/10610270500073796

M3 - Review article

SN - 1061-0278

VL - 17

SP - 369

EP - 375

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

IS - 5

ER -

Synthesis and properties of chiral molecular clefts related to Tröger's base

Abstract

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