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

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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, 2‐bromostyrene, 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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Enantiospecific Syntheses of Congested Atropisomers through Chiral Bis (aryne) Synthetic Equivalents ; day:29 ; month:09 ; year:2022 ; extent:1
Chemistry - a European journal ; (29.09.2022) (gesamt 1)

Creator: Dauvergne, Guillaume
Naubron, Jean‐Valère
Giorgi, Michel
Bugaut, Xavier
Rodriguez, Jean
Carissan, Yannick
Coquerel, Yoann

DOI: 10.1002/chem.202202473

URN: urn:nbn:de:101:1-2022092915065293583064

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:22 AM CEST

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Associated

Dauvergne, Guillaume
Naubron, Jean‐Valère
Giorgi, Michel
Bugaut, Xavier
Rodriguez, Jean
Carissan, Yannick
Coquerel, Yoann

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

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