90-39-1
Chemical Structure
(-)-Sparteine
Synonym(s): (-)-Lupinidine
- CAS No.: 90-39-1
- Formula:C15H26N2
- Molecular Weight:234.39
IUPAC Name: (7S,7aR,14S,14aS)-dodecahydro-2H,6H-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocine
InChIKey: SLRCCWJSBJZJBV-ZQDZILKHSA-N
SMILES: [H][C@]12CCCCN1C[C@H]3[C@]4([H])CCCCN4C[C@@H]2C3
Biological Activity: (-)-Sparteine ((-)-Lupinidine) is a chiral proton base and catalytic promoter. (-)-Sparteine promotes the enantioselective carbolithiation of cinnamyl derivatives with primary and secondary organolithium reagents. (-)-Sparteine forms mixed aggregates with lithium halides. As an exogenous chiral base, (-)-Sparteine deprotonates palladium-bound secondary alcohols, promotes the formation of palladium-alkoxide species, and alters the rate-limiting step of the catalytic cycle, thereby affecting reaction rate and enantioselectivity[1][2].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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(-)-Sparteine | 99.89% | (-)-Sparteine ((-)-Lupinidine) is a chiral proton base and catalytic promoter. (-)-Sparteine promotes the enantioselective carbolithiation of cinnamyl derivatives with primary and secondary organolithium reagents. (-)-Sparteine forms mixed aggregates with lithium halides. As an exogenous chiral base, (-)-Sparteine deprotonates palladium-bound secondary alcohols, promotes the formation of palladium-alkoxide species, and alters the rate-limiting step of the catalytic cycle, thereby affecting reaction rate and enantioselectivity. | ||||||||||||||||||||
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References
- [1]. Klein, Sophie, et al. Asymmetric carbolithiation of cinnamyl derivatives in the presence of (-)-sparteine." Journal of the American Chemical Society 117.34 (1995): 8853-8854.
- [2]. Mueller JA, et al. Mechanistic investigations of the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols using (-)-sparteine. Journal of the American Chemical Society. 2003 Jun 11;125(23):7005-13.
