Highly Enantioselective Michael Addition of Malonates to β-CF3-β-(3-Indolyl)nitroalkenes: Construction of Trifluoromethylated All-Carbon Quaternary Stereogenic Centres

A family of γ-nitrobutyric acid esters bearing an all-carbon quaternary stereogenic centre have been synthesized. Chiral thioureas catalysed the conjugate addition of malonates to nitroalkenes containing a trifluoromethyl and indole motif at the β-position to afford the corresponding γ-nitrobutyric acid esters in good yields (up to 89 % yield) and with good to excellent enantioselectivities (up to 90 % ee). This protocol provides an efficient access to optically enriched γ-amino acids and β-disubstituted γ-butyrolactams.