ReportsChemistry

Copper-catalyzed asymmetric addition of olefin-derived nucleophiles to ketones

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Science  08 Jul 2016:
Vol. 353, Issue 6295, pp. 144-150
DOI: 10.1126/science.aaf7720

Olefins enlisted to attack ketones

The reaction of C=O groups in ketones with organometallic compounds is a common method to form carbon-carbon bonds. One drawback to this approach, however, is that the organometallics, such as magnesium-derived Grignard reagents, are difficult to handle and susceptible to side reactions. Yang et al. present an alternative method, whereby a copper catalyst activates stable olefins (C=C double bonds) to attack ketones at room temperature. An added silane functions as a reducing agent, and a chiral phosphine ligand renders the reaction highly enantioselective.

Science, this issue p. 144