Enantiospecific Syntheses of Congested Atropisomers through Chiral Bis(aryne) Synthetic Equivalents - Aix-Marseille Université Access content directly
Journal Articles Chemistry - A European Journal Year : 2022

Enantiospecific Syntheses of Congested Atropisomers through Chiral Bis(aryne) Synthetic Equivalents

Abstract

The synthetic equivalents of the enantiopure binaphthyl bis(aryne) atropisomers derived from BINOL (1,1'bi-2,2'-naphtol) featuring a stereogenic axis vicinal to the two reactive triple bonds can be generated for the first time in solution in an enantiospecific manner. Using a two-step sequence based on the bidirectional [4+2] cycloaddition of furan derivatives followed by an aromatizative deoxygenation reaction, several 9,9'-bianthracenyl-based atropisomers could be prepared enantiospecifically in high enantiomeric purity. Alternatively, bidirectional reactions with anthracene, 2bromostyrene, and perylene as the arynophiles afforded very congested bis(benzotriptycene), bis(tetraphene) and bis(anthra[1,2,3,4-ghi]perylene) nanocarbon atropisomers in equally high enantiomeric purity. In complement, cross reactions with two different arynophiles revealed possible. The unusual atropisomer prototypes described in this study open the way to enantiopure nanographene atropisomers designed for functions.
Fichier principal
Vignette du fichier
2022CEJ.pdf (4.65 Mo) Télécharger le fichier
Origin : Publication funded by an institution

Dates and versions

hal-03856902 , version 1 (17-11-2022)

Licence

Attribution

Identifiers

Cite

Guillaume Dauvergne, Jean‐valère Naubron, Michel Giorgi, Xavier Bugaut, Jean Rodriguez, et al.. Enantiospecific Syntheses of Congested Atropisomers through Chiral Bis(aryne) Synthetic Equivalents. Chemistry - A European Journal, 2022, pp.e202202473. ⟨10.1002/chem.202202473⟩. ⟨hal-03856902⟩

Relations

37 View
8 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More