One, two, three, four: twist! Four consecutive (one-pot) electrophilic sulfur insertions on triarylamines with phthalimidesulfenyl chloride (see scheme), offer an easy access to chiral hetero[4]- and -[6]helicenes that are remarkably stable against a reversal of the helicity. These heterohelicenes were resolved by HPLC on an amylose-based chiral stationary phase, and the absolute configuration was established by ab initio calculations and experimental vibrational circular dichroism spectra.

Efficient Thia-Bridged Triarylamine Heterohelicenes: Synthesis, Resolution, and Absolute Configuration Determination / G., Lamanna; C., Faggi; Gasparrini, Francesco; Ciogli, Alessia; Villani, Claudio; P. J., Stephens; F. J., Devlin; S., Menichetti. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - STAMPA. - 14:(2008), pp. 5747-5750. [10.1002/chem.200800705]

Efficient Thia-Bridged Triarylamine Heterohelicenes: Synthesis, Resolution, and Absolute Configuration Determination.

GASPARRINI, Francesco;CIOGLI, Alessia;VILLANI, Claudio;
2008

Abstract

One, two, three, four: twist! Four consecutive (one-pot) electrophilic sulfur insertions on triarylamines with phthalimidesulfenyl chloride (see scheme), offer an easy access to chiral hetero[4]- and -[6]helicenes that are remarkably stable against a reversal of the helicity. These heterohelicenes were resolved by HPLC on an amylose-based chiral stationary phase, and the absolute configuration was established by ab initio calculations and experimental vibrational circular dichroism spectra.
2008
aromatic substitution; chiral resolution; heterohelicenes; sulfur heterocycles; vibrational circular dichroism
01 Pubblicazione su rivista::01a Articolo in rivista
Efficient Thia-Bridged Triarylamine Heterohelicenes: Synthesis, Resolution, and Absolute Configuration Determination / G., Lamanna; C., Faggi; Gasparrini, Francesco; Ciogli, Alessia; Villani, Claudio; P. J., Stephens; F. J., Devlin; S., Menichetti. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - STAMPA. - 14:(2008), pp. 5747-5750. [10.1002/chem.200800705]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/229132
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