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Direct assignment of the relative configuration in acyclic 1,3-diols by 1H NMR spectroscopy.

Anderson CE, Britt DK, Sangji S, O'Leary DJ, Anderson CD, Rychnovsky SD

Department of Chemistry, Pomona College, Claremont, California 91711, USA.

[chemical reaction: see text]. Using an operationally simple deuterium isotopic perturbation method, the relative configuration of 1,3-diols can be determined directly using 1H NMR spectroscopy. A comparison of the OH chemical shifts for OH/OH and OH/OD isotopomers provides a reliable assessment of the relative configuration of the diol; anti-1,3-diols within polyacetate and polypropionate frameworks have upfield isotope shifts of 2-16 ppb, whereas syn-1,3-diols show upfield isotope shifts of 20-33 ppb.

Published 2 December 2005 in Org Lett, 7(25): 5721-3.
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