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Letter

Direct Assignment of the Relative Configuration in Acyclic 1,3-Diols by ¹H NMR Spectroscopy

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Carolyn E. Anderson, David K. Britt, Sheharbano Sangji, and Daniel J. O'Leary*

Department of Chemistry, Pomona College, 645 N. College Avenue, Claremont, California 91711

Christopher D. Anderson and Scott D. Rychnovsky

Department of Chemistry, University of California-Irvine, 516 Rowland Hall, Irvine, California 92697

Org. Lett., 2005, 7 (25), pp 5721–5723

DOI: 10.1021/ol052539d

Publication Date (Web): November 9, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, doleary@pomona.edu

Abstract

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.

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History

Published In Issue December 08, 2005
Received October 20, 2005

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Letter

Direct Assignment of the Relative Configuration in Acyclic 1,3-Diols by ¹H NMR Spectroscopy