The Synthesis of Trianglimines: Scope and Limitations of the [3 + 3] Cyclocondensation Reaction Between (1R,2R)-Diaminocyclohexane and Aromatic Dicarboxaldehydes.

Abstract

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Probing the mechanism and dynamic reversibility of trianglimine formation using real‐time electrospray ionization time‐of‐flight mass spectrometry

“…[9,10] We have shown that trianglimines can be obtained from almost any synthetically accessible aromatic dialdehyde with complete control of the size of the macrocycle and functionalities incorporated into the aromatic moiety. [10][11][12][13][14] More importantly, we have demonstrated that trianglimines can be incorporated into more sophisticated structures such as catenanes and shown their promise in chiral recognition. [15,16] Trianglimines are characterized by their structural diversity, ease of synthesis in quantitative yields and most importantly by their chirality, where both enantiomers of any derivative are readily available in a pure form.…”

“…Trianglamines are readily synthesized in quantitative yields by reducing trianglimines with sodium borohydride . We have shown that trianglimines can be obtained from almost any synthetically accessible aromatic dialdehyde with complete control of the size of the macrocycle and functionalities incorporated into the aromatic moiety . More importantly, we have demonstrated that trianglimines can be incorporated into more sophisticated structures such as catenanes and shown their promise in chiral recognition .…”

“…More importantly, we have demonstrated that trianglimines can be incorporated into more sophisticated structures such as catenanes and shown their promise in chiral recognition . Trianglimines are characterized by their structural diversity, ease of synthesis in quantitative yields and most importantly by their chirality, where both enantiomers of any derivative are readily available in a pure form . Recently, we reported a novel functionalization approach for the synthesis of regioisomeric C 3 ‐symmetrical and non‐symmetrical trianglimines .…”

“…[15,16] Trianglimines are characterized by their structural diversity, ease of synthesis in quantitative yields and most importantly by their chirality, where both enantiomers of any derivative are readily available in a pure form. [9][10][11][12][13][14][15][16][17] Recently, we reported a novel functionalization approach for the synthesis of regioisomeric C 3 -symmetrical and non-symmetrical trianglimines. [18] We showed also that ESI-TOF (electrospray ionization time-of-flight) mass spectrometry (MS) could be used as a sophisticated technique for monitoring the progress of the [3+3]-cyclocondensation reactions.…”

Probing the dynamic reversibility and generation of dynamic combinatorial libraries in the presence of bacterial model oligopeptides as templating guests of tetra‐carbohydrazide macrocycles using electrospray mass spectrometry

“…In terms of DCL building blocks we have chosen aromatic dialdehydes in combination with dihydrazides based on tartaric acid. We have shown that dialdehydes in combination with diamines are able to form trianglimine macrocycles allowing large variability in the dialdehyde building block . Recently, we have shown that using real‐time mass spectrometry (MS), we could detect all intermediates in a DCL formation along with probing the dynamic reversibility of the process .…”