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

TY - JOUR

T1 - Revisiting the sparteine surrogate

T2 - Development of a resolution route to the (-)-sparteine surrogate

AU - Firth, James D.

AU - O'Brien, Peter

AU - Ferris, Leigh

PY - 2014/12/14

Y1 - 2014/12/14

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84908610696&partnerID=8YFLogxK

U2 - 10.1039/c4ob01694g

DO - 10.1039/c4ob01694g

M3 - Article

AN - SCOPUS:84908610696

SN - 1477-0520

VL - 12

SP - 9357

EP - 9365

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 46

ER -