title: Revisiting the sparteine surrogate: development of a resolution route to the (-)-sparteine surrogate.
abstract: The improved performance of the sparteine surrogate compared to sparteine in a range of applications has highlighted the need to develop an approach to the (-)-sparteine surrogate, previously inaccessible in gram-quantities. A multi-gram scale, chromatography-free synthesis of the racemic sparteine surrogate and its resolution via diastereomeric salt formation with (-)-O,O'-di-p-toluoyl-l-tartaric acid is reported. Resolution on a 10.0 mmol scale gave the diastereomeric salts in 33% yield from which (-)-sparteine surrogate of 93 : 7 er was generated. This work solves a key limitation: either enantiomer of the sparteine surrogate can now be readily accessed.
authors.affiliation: Department of Chemistry, University of York, Heslington, York YO10 5DD, UK. peter.obrien@york.ac.uk.
authors.forename: James D
authors.initials: JD
authors.lastname: Firth
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien
authors.forename: Leigh
authors.initials: L
authors.lastname: Ferris
mesh_terms: D015394:Molecular Structure; D012997:Solvents; D013034:Sparteine / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
chemical_list: D012997:Solvents; D013644:Tartrates; C422602:di-p-toluoyltartaric acid; D013034:Sparteine