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

Autor: Guillaume Dauvergne, Jean‐Valère Naubron, Michel Giorgi, Xavier Bugaut, Jean Rodriguez, Yannick Carissan, Yoann Coquerel
Přispěvatelé: Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Fédération Sciences Chimiques Marseille (FSCM)
Rok vydání: 2022
Předmět:
Zdroj: Chemistry-A European Journal
Chemistry-A European Journal, 2022, pp.e202202473. ⟨10.1002/chem.202202473⟩
ISSN: 1521-3765
0947-6539
DOI: 10.1002/chem.202202473
Popis: International audience; 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.
Databáze: OpenAIRE
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