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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
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