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

Vincent, Adrien, Deschamps, Damien, Martzel, Thomas, Lohier, Jean -Francois, Richards, Christopher J., Gaumont, Annie-Claude and Perrio, Stephane (2016) Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary. Journal of Organic Chemistry, 81 (9). pp. 3961-3966. ISSN 0022-3263

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Abstract

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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Pure Connector
Date Deposited: 10 Jun 2016 11:00
Last Modified: 10 Jun 2020 23:59
URI: https://ueaeprints.uea.ac.uk/id/eprint/59288
DOI: 10.1021/acs.joc.6b00560

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