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Revisiting the sparteine surrogate: development of a resolution route to the (-)-sparteine surrogate
James D Firth1, Peter O'Brien, Leigh Ferris
1Department of Chemistry, University of York, Heslington, York YO10 5DD, UK. peter.obrien@york.ac.uk.
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.
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