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

Abstract

AbstractA 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.