Isotopic Desymmetrisation as a Stereochemical Probe

Molecular symmetry can sometimes be a major impediment to the elucidation of stereochemical information. In certain cases, the appropriate placement of a stable isotope (e.g. ²H, ¹³C and ¹⁸O) can allow isotopic desymmetrisation with only minor perturbations in reactivity relative to the unlabelled compound. Memory effects in palladium-catalysed allylic alkylation and N-chiral proton sponges are two such cases in which isotopic desymmetrisation may be employed with minimal effort and with great effect.

stable isotopes - Pd-allyl complexes - proton sponges - NMR