Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary

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 dev...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-05, Vol.81 (9), p.3961-3966
Main Authors: Vincent, Adrien, Deschamps, Damien, Martzel, Thomas, Lohier, Jean-François, Richards, Christopher J, Gaumont, Annie-Claude, Perrio, Stéphane
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary: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 (∼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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00560