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Synfacts 2011(2): 0186-0186  
DOI: 10.1055/s-0030-1259263
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Asymmetric Allylic Substitution with Arylaluminum Reagents

Contributor(s): Hisashi Yamamoto, Patrick Brady
F. Gao, Y. Lee, K. Mandai, A. H. Hoveyda*
Boston College, Chestnut Hill, USA
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

This work describes a highly efficient enantioselective allylic substitution of allyl phosphates. The reaction is catalyzed by an in situ generated copper-NHC complex and employs nucleophilic arylaluminum reagents, which are conveniently prepared from the corresponding aryllithium reagent. Chiral quaternary stereogenic centers are produced from readily available starting materials.