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Sparteines as Chiral Ligands for Asymmetric Synthesis
No.159(October 2013)
The alkaloid (−)-sparteine (1) has found widespread use as a chiral ligand for asymmetric reactions.1) The complex formed from 1 and organolithium has recognized enantiotopic sides in its carbanions and prochiral reaction partner’s protons.2,3) Asymmetric aldol additions using 1 and TiCl4 have provided aldol products with excellent chiral selectivities.4) Palladium-catalyzed oxidation and the following resolutions of secondary alcohols assisted by 1 as a ligand have provided the optically activated alcohols.5) In addition, 1 has been used for enantiomer-selective polymerizations.6)
(+)-Sparteine (2) is not easily obtained from natural source compared with 1. However, 2 has potential for a chiral ligand which affords the products having an opposite configuration to those obtained by using 1.3)
References
- 1)Review of (−)-sparteine as a chiral ligand for metal catalysts
- 2)Review of enantioselective synthesis with Li/(−)-sparteine carbanion pairs
- 3)Asymmetric lithiation of (−)-sparteine and (+)-sparteine
- 4)Asymmetric aldol additions using (−)-sparteine and TiCl4
- 5)Palladium-catalyzed oxidative kinetic resolutions of secondary alcohols with (−)-sparteine
- 6)Enantiomer-selective polymerizations using (−)-sparteine
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