Planar Chirality of Imidazole‐Containing Macrocycles – Understanding and Tuning Atropisomerism

Berge, Emilie Van Den; Pospíšil, Jiří; Trieu-Van, Tran; Collard, Laurent; Robiette, Raphaël

doi:10.1002/ejoc.201100805

Cited by 21 publications

(10 citation statements)

References 33 publications

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“…Similarly, 15- to 18-membered ring macrocycles that incorporate an imidazole group were synthesized using a RCM of the corresponding dienes using GII as the catalyst ( Scheme 25 ) [ 64 – 66 ].…”

Section: Reviewmentioning

confidence: 99%

Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics

Lafaye¹,

Bosset²,

Nicolas³

et al. 2015

Beilstein J. Org. Chem.

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SummaryAlkenes containing N-heteroaromatics are known to be poor partners in cross-metathesis reactions, probably due to catalyst deactivation caused by the presence of a nitrogen atom. However, some examples of ring-closing and cross-metathesis involving alkenes that incorporate N-heteroaromatics can be found in the literature. In addition, recent mechanistic studies have focused on the rationalization of nitrogen-induced catalysts deactivation. The purpose of this mini-review is to give a brief overview of successful metathesis reactions involving olefins containing N-heteroaromatics in order to delineate some guidelines for the use of these challenging substrates in metathesis reactions.

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Section: Reviewmentioning

confidence: 99%

Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics

Lafaye¹,

Bosset²,

Nicolas³

et al. 2015

Beilstein J. Org. Chem.

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“…Van Den Berge et al also used principally the same method to elaborate other 5-aryl-1 H -imidazole-containing macrocycles 8 – 10 by varying the size cavity ( Figure 3 ) [ 18 ]. They found that the cyclisation step yield increased with an increase in the chain length.…”

Section: Synthesis Of Imidazolic Macrocyclesmentioning

confidence: 99%

Insights on the Synthesis of N-Heterocycles Containing Macrocycles and Their Complexion and Biological Properties

et al. 2022

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Macrocyclic chemistry has been extensively developed over the past several decades. In fact, the architecture of new macrocyclic models has undergone exponential growth to offer molecules with specific properties. In this context, an attempt is made in this study to provide an overview of some synthetic methods allowing the elaboration of N-heterocycles containing macrocycles (imidazole, triazole, tetrazole, and pyrazole), as well as their applications in the complexation of metal cations or as pharmacological agents.

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“…Finally, the imidazole nucleus has also been used to elaborate C–C ‐bonded atropisomeric 15‐ and 16‐membered macrocycles 20a and 20b from precursor 19 by ring‐closing metathesis followed by hydrogenation. These macrocycles 20a and 20b show high barriers to rotation of 170.9 and 109.5 kJ mol –1 , corresponding to half‐lives of racemization at 25 °C of several trillion years and 40 days, respectively (Scheme ) …”

Section: Non‐stereoselective Synthesesmentioning

confidence: 99%

A Bird's Eye View of Atropisomers Featuring a Five‐Membered Ring

2018

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An atropisomer is a member of a subclass of restricted rotational conformers – this restricted rotation giving rise to stereogenic sigma bonds – that can be isolated as separate chemical species. Most atropisomer are six‐membered‐ring biaryl or heterobiaryl derivatives. The aim of this microreview is to shed light on a less common class of atropisomers, those containing at least one five‐membered hetero‐ or carbocycle and displaying variously a stereogenic C–N, C–C, or even N–N chemical bond. After a short introduction, the occurrence of atropisomers in nature is presented, as well as the synthetic efforts – encompassing non‐stereoselective and diastereoselective strategies, together with an update on very recent enantioselective approaches – devoted to such axially chiral compounds. Finally, a special focus is placed on their important utilization as original and efficient ligands for metal complexes.

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Planar Chirality of Imidazole‐Containing Macrocycles – Understanding and Tuning Atropisomerism

Cited by 21 publications

References 33 publications

Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics

Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics

Insights on the Synthesis of N-Heterocycles Containing Macrocycles and Their Complexion and Biological Properties

A Bird's Eye View of Atropisomers Featuring a Five‐Membered Ring

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