Issue 46, 2014

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.

Graphical abstract: Revisiting the sparteine surrogate: development of a resolution route to the (−)-sparteine surrogate

Supplementary files

Article information

Article type
Paper
Submitted
07 8 2014
Accepted
25 9 2014
First published
25 9 2014

Org. Biomol. Chem., 2014,12, 9357-9365

Author version available

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

J. D. Firth, P. O'Brien and L. Ferris, Org. Biomol. Chem., 2014, 12, 9357 DOI: 10.1039/C4OB01694G

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