title: Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary.
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.
authors.affiliation: Normandie Univ, LCMT, ENSICAEN, UNICAEN, CNRS, 14000 Caen, France. Full address: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN & Université de Caen-Normandie , 14050 Caen, France.
authors.forename: Adrien
authors.initials: A
authors.lastname: Vincent
authors.affiliation: Normandie Univ, LCMT, ENSICAEN, UNICAEN, CNRS, 14000 Caen, France. Full address: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN & Université de Caen-Normandie , 14050 Caen, France.
authors.forename: Damien
authors.initials: D
authors.lastname: Deschamps
authors.affiliation: Normandie Univ, LCMT, ENSICAEN, UNICAEN, CNRS, 14000 Caen, France. Full address: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN & Université de Caen-Normandie , 14050 Caen, France.
authors.forename: Thomas
authors.initials: T
authors.lastname: Martzel
authors.affiliation: Normandie Univ, LCMT, ENSICAEN, UNICAEN, CNRS, 14000 Caen, France. Full address: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN & Université de Caen-Normandie , 14050 Caen, France.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Lohier
authors.affiliation: School of Chemistry, University of East Anglia , Norwich Research Park, Norwich, NR4 7TJ, U.K.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Richards
authors.affiliation: Normandie Univ, LCMT, ENSICAEN, UNICAEN, CNRS, 14000 Caen, France. Full address: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN & Université de Caen-Normandie , 14050 Caen, France.
authors.forename: Annie-Claude
authors.initials: AC
authors.lastname: Gaumont
authors.affiliation: Normandie Univ, LCMT, ENSICAEN, UNICAEN, CNRS, 14000 Caen, France. Full address: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN & Université de Caen-Normandie , 14050 Caen, France.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Perrio