Cu-Catalyzed Enantioselective Allylic Substitution with Grignard Reagents

Significance

The enantioselective allylic alkylation is well developed for soft nucleophiles like malonates, while the use of organometallic reagents for this reaction has not attracted much attention. However, this reaction is a versatile catalytic method for the creation of a tertiary asymmetric center. Usually, very high enantioselectivities and regioselectivities are achieved with only 1 mol% of the catalyst loading. Various primary alkylmagnesium halides react successfully. The products were also subjected to metathesis reactions with acrylic esters followed by diaste­reoselective Michael addition.