Copper-Catalyzed Asymmetric Allylic Substitution

Significance

Alexakis has found a very practical synthesis of enantioenriched functional compounds. Using commercially available 1,4-bishalo-2-butenes (mixture of stereoisomers) and Grignard reagents under copper catalysis, 100% γ-selectivity and ee values up to 94% can be obtained. The products of these reactions are very useful in that they contain a terminal olefin, a primary halide as well as the functionality brought by the Grignard reagent. This allows for a large number of subsequent transformations.