299-39-8
Chemical Structure
(-)-Sparteine sulfate
Synonym(s): (-)-Lupinidine sulfate
- CAS No.: 299-39-8
- Formula:C15H28N2O4S
- Molecular Weight:332.46
IUPAC Name: (7S,7aR,14S,14aS)-dodecahydro-2H,6H-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocine sulfate
InChIKey: FCEHFCFHANDXMB-UMEYXWOPSA-N
SMILES: [H][C@@]1(CN2CCCC[C@]32[H])C[C@@]3([H])CN4CCCC[C@@]14[H].O=S(O)(O)=O
Biological Activity: (-)-Sparteine sulfate ((-)-Lupinidine sulfate) is a chiral proton base and catalytic promoter. (-)-Sparteine sulfate promotes the enantioselective carbolithiation of cinnamyl derivatives with primary and secondary organolithium reagents. (-)-Sparteine sulfate forms mixed aggregates with lithium halides. As an exogenous chiral base, (-)-Sparteine sulfate 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].
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(-)-Sparteine sulfate | (-)-Sparteine sulfate ((-)-Lupinidine sulfate) is a chiral proton base and catalytic promoter. (-)-Sparteine sulfate promotes the enantioselective carbolithiation of cinnamyl derivatives with primary and secondary organolithium reagents. (-)-Sparteine sulfate forms mixed aggregates with lithium halides. As an exogenous chiral base, (-)-Sparteine sulfate 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.
