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Synfacts 2011(8): 0855-0855  
DOI: 10.1055/s-0030-1260817
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Asymmetric Allylic Alkylation with Organolithium Reagents

Contributor(s): Hisashi Yamamoto, Zhi Li
M. Pérez, M. Fañanás-Mastral, P. H. Bos, A. Rudolph, S. R. Harutyunyan*, B. L. Feringa*
University of Groningen, The Netherlands
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

This report describes the utilization of organolithium reagents as nucleophile sources in copper-catalyzed asymmetric allylic alkylation. Using Taniaphos as the chiral ligand, various alkyllithium reagents are nicely coupled with substituted allyl bromides in SN2′ manner. Using a chiral phosphoramidite ligand allows cinnamyl chloride and phenyllithium to participate in the reaction.