Enantiomerically pure [2.2]paracyclophane-4-thiol: A planar chiral sulfur-based building block readily available by resolution with an amino acid chiral auxiliary

Adrien Vincent, Damien Deschamps, Thomas Martzel, (Jean-François Lohier, Christopher J. Richards, Annie-Claude Gaumont, Stéphane Perrio

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Acyl chloride of N-phthaloyl-(S)-isoleucine is an efficient chiral auxiliary for the resolution of (+/-)-[2.2]paracyclophane-4-thiol. A preparative protocol, based on the conversion into diastereoisomeric thiolesters and separation by two fractional crystallizations and column chromatography, was developed. Deprotection with LiAlH4 allowed isolation of the individual thiol enantiomers in good yield (similar to 40%) and high enantiomeric purity (ee >93%). The absolute configurations were determined by comparison of the optical rotation value of the products with literature data and were confirmed by X-ray crystallography.

Original languageEnglish
Pages (from-to)3961-3966
Number of pages6
JournalJournal of Organic Chemistry
Issue number9
Early online date15 Apr 2016
Publication statusPublished - 5 Jun 2016

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