Synthesis of a Bolm's 2,2′-Bipyridine Ligand Analogue and Its Applications - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2018

Synthesis of a Bolm's 2,2′-Bipyridine Ligand Analogue and Its Applications

Résumé

A new method of synthesis of an analogue of Bolm's 2,2'-bipyridine ligand based on the catalytic [2 + 2 + 2] cyclotrimerization of 1-halodiynes with nitriles was developed. Crucial step of the whole synthesis turned out to be homodimerization of a substituted 2-bromopyridine to the corresponding bipyridine, that was studied and optimized. The newly prepared bipyridine (S,S)-2 was then tested as a chiral ligand in metalcatalyzed enantioselective reactions. Out of the studied reactions the most promising results were obtained in epoxide ring opening (82% yield, 98% ee) and Mukaiyama aldol reaction (> 96% yield, 99/1 dr, 92% ee). In the case of Mukaiyama-aldol reaction as well as in the Michael addition, novel ligand 2 proved its robustness compared to Bolm's ligand as it was less sensitive to the purity of used reagents.

Domaines

Chimie
Fichier principal
Vignette du fichier
Hal-129-2018.pdf (3.82 Mo) Télécharger le fichier
Origine Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-02370736 , version 1 (17-12-2020)

Identifiants

Citer

Eva Bednářová, Martin Dračínský, Štefan Malatinec, Ivana Císařová, Frédéric Lamaty, et al.. Synthesis of a Bolm's 2,2′-Bipyridine Ligand Analogue and Its Applications. Advanced Synthesis and Catalysis, 2018, 360 (15), pp.2869-2878. ⟨10.1002/adsc.201800452⟩. ⟨hal-02370736⟩
39 Consultations
138 Téléchargements

Altmetric

Partager

Gmail Mastodon Facebook X LinkedIn More