Current Tröger's Base Chemistry

@article{Dolensk2007CurrentTB,
  title={Current Tr{\"o}ger's Base Chemistry},
  author={B. Dolensk{\'y} and J. Elguero and V. Král and C. Pardo and Martin Val{\'i}k},
  journal={Advances in Heterocyclic Chemistry},
  year={2007},
  volume={93},
  pages={1-56}
}
Publisher Summary This chapter summarizes Troger's bases (TBs). It describes its historical developments, revival, synthesis and mechanism of formation, reactivity, physicochemical properties, and its uses and applications. The chapter also provides a brief discussion about pseudo-TBs. It is observed that in principle, any aromatic or heteroaromatic amine can serve as a possible precursor of TBs. TB derivatives are generally viewed as anomalous chiral substances with two nitrogen-containing… Expand
Design and synthesis of Tröger's base ditopic receptors: host-guest interactions, a combined theoretical and experimental study.
TLDR
Two flexible Tröger's base ditopic receptors C4TB and C5TB incorporating monoaza crown ether were designed and synthesized for bisammonium ion complexation and showed the highest affinity for the receptors. Expand
Synthesis and characterisation of a new naphthalene tris-Tröger’s base derivative—a chiral molecular clip
Serial tris-Troger’s base derivatives (trisTBs) are members of a recently introduced family of chiral molecular clips. Naphthalene tris-Troger’s base is prepared via both stepwise and one-potExpand
The first direct synthesis of chiral Tröger’s bases catalyzed by chiral glucose-containing pyridinium ionic liquids
Troger's base (TB) and its derivatives, especially chiral TBs are widely used in many fields. Although there is an urgent demand for the direct synthesis of pure enantiomers of TBs, convenientExpand
Functionalized analogues of Tröger's base: scope and limitations of a general synthetic procedure and facile, predictable method for the separation of enantiomers
Abstract A major stumbling block in the applications of enantiomerically pure Troger's base analogues is their poor availability. We have therefore developed a facile method for the enantioseparationExpand
Simple dissymmetrical and asymmetrical Tröger's bases: photophysical and structural characterization
Despite their continuously growing preparation and applications in the last few decades, the photophysical properties of Troger's bases (TBs) with small substituents have not been analyzed. WeExpand
Synthesis and biological activity evaluation of hydrazone derivatives based on a Tröger's base skeleton.
TLDR
Evaluation of the anticancer activity of these agents using seven cancer cell lines and two healthy cell lines found that several derivatives had potent anticancers activity and excellent selectivity indexes toward cancer cells. Expand
Innovative Multipodal Ligands Derived from Tröger's Bases for the Sensitization of Lanthanide(III) Luminescence.
TLDR
The geometry and the substitution pattern of the ligands allow the control of the stoichiometry of the species formed and the Tb(III) luminescence sensitization efficiency, showing that para -substitution patterns are more efficient than meta - Substitution ones for the formation of coordination compounds with lower T b(III)/ligand ratio. Expand
Structures of alkyl-substituted Tröger's base derivatives illustrate the importance of Z' for packing in the absence of strong crystal synthons.
TLDR
Crystal structures of Tröger's base analogues with the methyl groups replaced by ethyl, iso-propyl and tert-butyl groups were studied and the incidence of Z' > 1 structures increases to rather conspicuous levels. Expand
Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part II
Seven racemic derivatives of Troger’s base—the 1,7-dibromo-substituted derivative 3, the 2,8-dibromo-substituted derivative 4, the 2,8-diiodo-substituted derivative 5, the 3,9-diiodo-substitutedExpand
Efficient Intersystem Crossing in Tröger's Base Derived From 4-Amino-1,8-Naphthalimide and Application as Potent PDT Reagent.
Intersystem crossing (ISC) was observed for naphthalimide-derived Tröger's base, and the ISC is confirmed as spin orbital charge transfer ISC (SOCT-ISC) mechanism. Conventional electronExpand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 212 REFERENCES
The Chemistry of a Non‐Natural Product: Troeger′s Base
Troger's base was the first amine to be resolved where the chirality was solely due to very high inversion barrier around nitrogen atom(s). Though the molecule was known over a century, work doneExpand
Preparation of Troger Base Derivatives by Cross-Coupling Methodologies
Derivatives of the Troger base are finding increasing application in supramolecular chemistry: they are introduced as rigid scaffolds into synthetic receptors and 'molecular torsional balances' toExpand
Synthesis of Halogen Substituted Analogues of Tröger’s Base
Synthesis 2001, No. 12, 25 09 2001. Article Identifier: 1437-210X,E;2001,0,12,1873,1877,ftx,en;T03301SS.pdf. © Georg Thieme Verlag Stuttgart · New York ISSN 0039-7881 Abstract: Halogen substitutedExpand
Synthesis of functionalized chiral carbocyclic cleft molecules complementary to Tröger's base derivatives.
The synthesis of optically pure functionalized cleft molecules derived from dibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione is reported. These clefts are reminiscent of Tröger's base butExpand
Enantioselective Tröger's Base Synthetic Receptors☆
Abstract Synthetic receptors selective for the enantiomers of Troger's base ( 1 ), a compound containing chiral nitrogen atoms, have been prepared by the molecular imprinting of 1 in methacrylicExpand
A DFT study of the geometric, magnetic NMR chemical shifts and optical rotation properties of Tröger’s bases
Abstract A DFT computational study of Troger’s bases and related compounds (TBs) has been used to satisfactorily explain their geometry (including the flexibility aspect), the 1 H NMR chemical shiftsExpand
The synthesis and characterization of all diastereomers of a linear symmetrically fused Tris-Tröger's base analogue: new chiral cleft compounds.
TLDR
Each of the diastereomers 1 a-c is resistant to inversion at the stereogenic nitrogen atoms under strongly and weakly acidic conditions in the range from room temperature to 95 degrees C, which is unique for analogues of Tröger's base in general to date. Expand
Synthesis and Properties of Chiral Molecular Clefts Related to Tröger's Base
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 areExpand
Synthesis and molecular structure of heterocyclic Tröger's bases derived from C -amino heterocycles
Abstract Fourteen amino heterocycles were allowed to react in the different experimental conditions of formation of Troger's bases. Amino-azoles and -benzazoles yielded the corresponding Troger'sExpand
A New Entry to Bis‐Tröger’s Bases
This paper reports the use of p-phenylenediamine to prepare bis-Troger’s bases. The methyl,nitro-substituted bis-Troger’s base 5, already previously prepared by another procedure, was obtained inExpand
...
1
2
3
4
5
...