Table 1.

Evaluation of Reaction Conditions for the CuH-Catalyzed Allylation of 4-Methoxyacetophenone.^a

^aConditions: 0.2 mmol ketone (1 equiv), 1,3-butadiene (2 equiv), copper(II) acetate (0.05 equiv), ligand (0.06 equiv), dimethoxy(methyl)silane (4 equiv) in solvent (0.2 mL), ketone was added slowly by syringe pump; see the Supporting Information for details.

^bYield and diastereomeric ratio were determined by ¹H NMR spectroscopy of the crude mixture, using dibromomethane as an internal standard.

^cEnantiomeric ratio was determined by HPLC or SFC analysis on commercial chiral columns, and the relative configuration of 1 was determined by comparing its NMR data with reported data.¹⁷