Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary - Archive ouverte HAL Access content directly
Journal Articles Journal of Organic Chemistry Year : 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

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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 (∼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.

Dates and versions

hal-01830259 , version 1 (04-07-2018)

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Adrien Vincent, Damien Deschamps, Thomas Martzel, Jean-François Lohier, Christopher Richards, et al.. 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, 2016, 81 (9), pp.3961 - 3966. ⟨10.1021/acs.joc.6b00560⟩. ⟨hal-01830259⟩
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