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Sparteines as Chiral Ligands for Asymmetric Synthesis

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)


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