Synthesis of new chiral molecular tweezers with a tris-Tröger's base skeleton

Mas, Thierry; Pardo, Carmen; Elguero, José

doi:10.1070/mc2004v014n06abeh002016

Cited by 13 publications

(10 citation statements)

References 12 publications

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“…partial isomerization of the starting bisTB subunit occurred. 17 In contrast, troegeration with HMTA in TFA at rt for 72 h gave only syn,anti-7ah (in 46% yield) and syn,syn-7ah (in 19% yield), i.e. no isomerization of the starting bisTB subunits was observed.…”

Section: Linear Synthesis Of Tristbsmentioning

confidence: 96%

“…16 The estimation based on 1 H NMR was even supported by quantum chemical calculations, and was also successful in the case of Z-bisTB, 11 and partially validated for U-trisTB. 11,17,18 Scheme 1 General structure of TB derivatives, enantiomers of Tro¨ger's base (1a), and Reed's naphthalene TB 1b. Scheme 2 General structure of bisTB, and diastereoisomers of U-bisTB 2c.…”

Section: Bis Tro¨ger's Basesmentioning

confidence: 99%

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Oligo Tröger's bases—new molecular scaffolds

2012

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Oligo Tröger's bases are compounds containing two or more Tröger's base subunits (1,5-methanodiareno[b,f][1,5]diazocines) sharing one or more arene parts. Due to their interesting molecular shapes, these compounds are studied as chiral molecular tweezers, clips, cavitands, clefts, calixes, etc. This review includes all available data on oligo Tröger's bases, and introduces their preparation and properties to a wide audience.

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Section: Linear Synthesis Of Tristbsmentioning

confidence: 96%

Section: Bis Tro¨ger's Basesmentioning

confidence: 99%

Oligo Tröger's bases—new molecular scaffolds

2012

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“…In addition, we have synthesised the first example of a tetranitro Tröger's base analogue. We expect that these molecules will become useful building blocks, via conversion to the corresponding diamines, in the synthesis of more highly functionalised compounds such as bis-, [22][23][24][25] tris- [26][27][28] or higher-order fused Tröger's base analogues and in the synthesis of new double-stranded helicates. [10,29] …”

Section: Discussionmentioning

confidence: 99%

Synthesis of Symmetric Dinitro‐Functionalised Tröger's Base Analogues

et al. 2009

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The synthesis of six new examples of 2,8‐dinitro‐substituted Tröger's base analogues are reported, together with the first examples of 1,7‐, 3,9‐ and 4,10‐dinitro Tröger's base analogues and the first example of a tetranitro Tröger's base compound. Several of these dinitro compounds lack substituents at the 2‐ and 8‐positions and therefore provide further examples of Tröger's base analogues derived from anilines lacking a para substituent. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…8,9 Recently, Pardo and Kra ´l synthesized more extended analogues: fused tris-Tro ¨ger's bases (Figure 1). 10,11 There are three possible regioisomers of fused tris-Tro ¨ger's base analogues, the "nonsymmetric", the "nonlinear symmetric", and the "linear symmetric" (as shown for the fused tris-Tro ¨ger's base dibromo-anlogues in Figure 2). 12 In addition, for each of these regiosisomers there are three different possible diastereomers, syn-anti, anti-anti, and syn-syn.…”

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confidence: 99%