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Synlett 2001; 2001(2): 0161-0183
DOI: 10.1055/s-2001-10759
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Isotopic Desymmetrisation as a Stereochemical Probe

Guy C. Lloyd-Jones*
  • *School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK; Fax +44(117)929 8611; E-mail: guy.lloyd-jones§bristol.ac.uk
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Publication Date:
31 December 2001 (online)

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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

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