Application of NMR Spectroscopy for the Detection of Equilibrating E-Z Diastereomers

Conjugation can lower the energy barrier for unsaturated C-C bond rotations, resulting in a mixture of equilibrating diastereomers at room temperature. Therefore, methods claiming diastereoselective synthesis of conjugated double bonds often require proof that the observed diastereomeric ratio is not because of the diastereomeric equilibration of the product. Variable-temperature (VT) NMR experiments are commonly used to distinguish between the two possibilities. However, the VT technique requires accessories for the NMR spectrometer and more setup time. Here, we show that the rarely used application of 1-D and 2-D nuclear Overhauser effect spectroscopy experiments for the detection of the equilibrating diastereomers is a convenient alternative to the VT technique.