Direct assignment of the relative configuration in acyclic 1,3-diols by 1H NMR spectroscopy.
[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.
Anderson
Carolyn E
CE
Department of Chemistry, Pomona College, Claremont, California 91711, USA.
Britt
David K
DK
Sangji
Sheharbano
S
O'Leary
Daniel J
DJ
Anderson
Christopher D
CD
Rychnovsky
Scott D
SD
D000438:Alcohols / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols