Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy - Aix-Marseille Université Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2018

Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy

Résumé

[60]Fullerene and its rarely explored reversible covalent chemistry have been harnessed as an efficient alternative for the chiral resolution of racemates. By using only catalytic amounts of chiral agents, stereodivergent 1,3-dipolar cycloadditions of racemic helicenes onto [60]fullerene were carried out. The formed helicene/fullerene diastereomers were easily separated by conventional chromatography, and afterward, a simple catalyzed 1,3-dipolar retro-cycloaddition afforded helicene starting materials in high optical purity.

Domaines

Chimie organique
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Dates et versions

hal-01767767 , version 1 (16-04-2018)

Identifiants

Citer

Rosa M. Giron, Jiangkun Ouyang, Ludovic Favereau, Nicolas Vanthuyne, Jeanne Crassous, et al.. Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy. Organic Letters, 2018, 20 (7), pp.1764-1767. ⟨10.1021/acs.orglett.8b00256⟩. ⟨hal-01767767⟩
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