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Revisiting the sparteine surrogate: Development of a resolution route to the (-)-sparteine surrogate

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JournalOrganic and Biomolecular Chemistry
DateE-pub ahead of print - 25 Sep 2014
DatePublished (current) - 14 Dec 2014
Issue number46
Volume12
Number of pages9
Pages (from-to)9357-9365
Early online date25/09/14
Original languageEnglish

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 937 er was generated. This work solves a key limitation: either enantiomer of the sparteine surrogate can now be readily accessed.

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