The importance of Sparteine
Sparteine is a natural alkaloid widely used in materials and medicinal research in an industrial context, as attested by the numerous patents and scientific publications documenting its applications. In the past, the scientific community has faced Sparteine shortages, as documented here or here, highlighting the importance of this compound for both academic and industrial research. Although asymmetric total syntheses of Sparteine have been previously achieved, their multistep nature places them far from practical use.
We have developed a unique renewable process for the production of enantiomerically pure (-)- and (+)-Sparteine.
Selected applications of Sparteine in synthesis
Sparteine is an exceptional ligand for asymmetric lithiations, as demonstrated in the pioneering work by Hoppe.[1]
The enantioselective lithiation of N-Boc-pyrrolidine, originally reported by Beak, remains to this date as one of the most popular applications of Sparteine in synthesis.[2]
Beyond several applications in transition-metal catalysis,[3] a recent work by Aggarwal has reignited the pivotal role of Sparteine in asymmetric synthesis.[4]
References:
[1] D. Hoppe, T. Hense, Angew. Chem. Int. Ed. 1997, 36, 2282
[2] P. Beak, S. T. Kerrick, S. Wu, J. J. Chu, J. Am. Chem. Soc. 1994, 116, 3231
[3] O. Chuzel, O. Riant, Top. Organomet. Chem. 2005, 15, 59
[4] M. Burns, S. Essafi, J. R. Bame, S. P. Bull, M. P. Webster, S. Balieu, J. W. Dale, C. P. Butts, J. N. Harvey, V. K. Aggarwal, Nature 2014, 513, 183