Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of <i>Tröger</i>'s Base Analogues

Sergeyev, Sergey

doi:10.1002/hlca.200800329

Cited by 132 publications

(65 citation statements)

References 96 publications

(107 reference statements)

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“…These observations seemed auspicious, the expected reaction involving the substitution of a phosphine ligand by analogous carbene. However, after purification of the crude by column chromatograph on silica gel, 1 H-NMR and 13 C-NMR analyses performed on the white solid obtained revealed that we did not isolate the expected product. But it was a mixture of uncharacterized products.…”

Section: Thermolysis Tests Of Perhalogenated Adducts Of Tröger's Basementioning

confidence: 78%

“…Firstly, Tröger's base and its analogues (1a-d) were synthesized according to the method described in the litterature 13,15,18 . Thereafter, we proceeded on the removal of methylene bridge by using the method of Mahon 16 .…”

Section: Resultsmentioning

confidence: 99%

“…The Tröger's base has been synthesized in 1887 by Julius Tröger, but its structure was elucidated 38 years later by Vladimir Prelog and confirmed by X-ray diffraction in 1986 13 .…”

Section: Oriental Journal Of Chemistrymentioning

confidence: 99%

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Synthesis and NMR study of N-heterocyclic carbenes (NHC) precursors derived from Tröger’s Base

Musengimana

Fatakanwa²

2013

Orient. J. Chem

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Since the discovery of olefin metathesis reactions, various catalysts have been developed but those based on Ruthenium and N-heterocyclic carbenes (NHC) ligands are particularly more efficient. Herein, we report a synthesis of NHC precursors derived from the Tröger's base and its analogues which can be used in the synthesis of the new kind of metathesis catalysts. The NHC derived from the Tröger's base present a particular chirality that could affect stereoselectivity of catalysis, and the form "V" of these ligands implies that the aromatic substituents point totally outside the coordination sphere of the metal, where would be no steric hindrance unlike what happens with the usual NHC.

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Section: Thermolysis Tests Of Perhalogenated Adducts Of Tröger's Basementioning

confidence: 78%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and NMR study of N-heterocyclic carbenes (NHC) precursors derived from Tröger’s Base

Musengimana

Fatakanwa²

2013

Orient. J. Chem

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“…Since then, various of TB derivatives were synthesized and applied in the eld of molecular recognition [2], chiral ligands [3][4][5], DNA probes [6,7], stereo selective catalysis [8][9][10][11][12], drug development [13,14], CO 2 capture [15,16], bioorganic chemistry [17][18][19], electroluminescent materials [20,21] and supra molecular chemistry [22] in the last two decades. Their wide range of applications is based on their huge rigidity, V-shaped twisted con guration, N-central chirality and C 2 -symmetry.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1,1′-diformyl-4,4′-(6H,12H-5,11-methano-dibenzo[b,f][11,5]diazocine-2,8-diyl)dibenzene, C₂₉H₂₂N₂O₂

Qiu

Wan

Huang

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…After this period the reaction mixture was cooled to 0ºC, sat. NH 4 Cl added and the mixture warmed to room temperature. The reaction mixture then diluted with CH 2 Cl 2 and the combined organic layers were then washed with brine, dried (Na 2 SO 4 ), filtered and the solvent removed in vacuo.…”

Section: General Methods For Monoalkylationmentioning

confidence: 99%

The selective mono and difunctionalization of carbocyclic cleft molecules with pyridyl groups and X-ray crystallographic analysis

et al. 2010

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Citation: JILKA, P. ... et al, 2010. The selective mono and difunctionalization of carbocyclic cleft molecules with pyridyl groups and X-ray crystallographic analysis. Tetrahedron, 66 (48) --- IntroductionMolecular recognition relies on the ability to design and synthesize appropriate substrates with predictable geometries and binding sites. 1 Towards this end Tröger's base 2 1 has been used to great effect by a number groups within the context of molecular recognition because it contains a rigid predictable structure, heteroatoms capable of binding events and importantly a chiral cavity.3,4 While Tröger's base has proved effective as a chiral cleft molecule, a number of carbocyclic and heterocyclic analogues have also been also investigated as possible surrogates.5 The carbocyclic cleft molecule 2 was initially reported in 1960 by Stetter 6 but was fully characterized and resolved in 1975 by Tatemitsu et al. 7 Significant advances in the functionalization of 2 have been developed by the Harding group 8 and an excellent review on its development/ uses has been published (Figure 1). Of particular interest to our group is the reduced version of 2. Treatment of 2 with excess reducing agent results in the formation of the bis-hydroxyl carbocycle 3, where both hydroxyl groups are directed into the chiral cavity. This potentially gives a ligand which can bind substrates via metal or Brønsted base / acid binding interactions within a chiral cavity (Scheme 1). Scheme 1. Reduction of 2 to give diol 3.To date the only reported functionalization of these hydroxyl groups has been the attachment of simple esters (bromobenzoate, acetate and menthoxy acetyl) and the synthesis of cyclic ethers.7,10 The dibromobenzoate and diacetate derivatives were synthesized for characterization reasons, the dimenthoxy acetate was synthesized for separation purposes and the cyclic ethers A R T I C L E I N F O A B S T R A C TArticle history: Received Received in revised form Accepted Available onlineThe diesterification and selective mono and dialkylation of carbocyclic analogues of Tröger's base with pyridyl groups has been achieved in high yield and good selectivity giving access to a novel range of cleft molecules capable of binding events. Reaction conditions for the selective functionalization of this carbocyclic cleft molecule are discussed as well as the solid state structures of these newly synthesized ligands.

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Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

Cited by 132 publications

References 96 publications

Synthesis and NMR study of N-heterocyclic carbenes (NHC) precursors derived from Tröger’s Base

Synthesis and NMR study of N-heterocyclic carbenes (NHC) precursors derived from Tröger’s Base

Crystal structure of 1,1′-diformyl-4,4′-(6H,12H-5,11-methano-dibenzo[b,f][11,5]diazocine-2,8-diyl)dibenzene, C₂₉H₂₂N₂O₂

The selective mono and difunctionalization of carbocyclic cleft molecules with pyridyl groups and X-ray crystallographic analysis

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Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

Cited by 132 publications

References 96 publications

Synthesis and NMR study of N-heterocyclic carbenes (NHC) precursors derived from Tröger’s Base

Synthesis and NMR study of N-heterocyclic carbenes (NHC) precursors derived from Tröger’s Base

Crystal structure of 1,1′-diformyl-4,4′-(6H,12H-5,11-methano-dibenzo[b,f][11,5]diazocine-2,8-diyl)dibenzene, C29H22N2O2

The selective mono and difunctionalization of carbocyclic cleft molecules with pyridyl groups and X-ray crystallographic analysis

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Crystal structure of 1,1′-diformyl-4,4′-(6H,12H-5,11-methano-dibenzo[b,f][11,5]diazocine-2,8-diyl)dibenzene, C₂₉H₂₂N₂O₂