A Bird's Eye View of Atropisomers Featuring a Five‐Membered Ring. Issue 20 (25th April 2018)

• Record Type: Journal Article
• Authors: Bonne, Damien; Rodriguez, Jean
• Is Part Of: European journal of organic chemistry. Issue 20/21(2018)
• Page Start: 2417
• Page End: 2431
• Publication Date: 2018-04-25
• Subjects: Atropisomerism -- Five‐membered ring atropisomers -- Ligand design -- Natural products -- Organocatalysis -- Rotational barriers; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800078
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : The aim of this microreview is to shed light on a less common class of atropisomers, containing at least one five‐membered hetero‐ or carbocycle and displaying variously a stereogenic C–N, C–C, or even N–N chemical bond. Examples of such axially chiral molecules in nature and as ligands are presented, as well as their synthesis (stereoselective or not) .