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Assigning Stereochemistry to Single Diastereoisomers by GIAO NMR Calculation: The DP4 Probability

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Unilever Centre for Molecular Science Informatics, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
[email protected]
Cite this: J. Am. Chem. Soc. 2010, 132, 37, 12946–12959
Publication Date (Web):August 26, 2010
https://doi.org/10.1021/ja105035r
Copyright © 2010 American Chemical Society
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Abstract

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GIAO NMR shift calculation has been applied to the challenging task of reliably assigning stereochemistry with quantifiable confidence when only one set of experimental data are available. We have compared several approaches for assigning a probability to each candidate structure and have tested the ability of these methods to distinguish up to 64 possible diastereoisomers of 117 different molecules, using NMR shifts obtained in rapid and computationally inexpensive single-point calculations on molecular mechanics geometries without time-consuming ab initio geometry optimization. We show that a probability analysis based on the errors in each 13C or 1H shift is significantly more successful at making correct assignments with high confidence than are probabilities based on the correlation coefficient and mean absolute error parameters. Our new probability measure, which we have termed DP4, complements the probabilities obtained from our previously developed CP3 parameter, which applies to the case of assigning a pair of diastereoisomers when one has both experimental data sets. We illustrate the application of DP4 to assigning the stereochemistry or structure of 21 natural products that were originally misassigned in the literature or that required extensive synthesis of diastereoisomers to establish their stereochemistry.

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Derivations of eqs 3 and 4, complete details of calculated and experimental shifts, detailed results of assigning each of the molecules in Figure 1 using each of the parameters, expectation values and standard deviations for all of the parameters, and calculated geometries and energies for all the molecules studied. This material is available free of charge via the Internet at http://pubs.acs.org.

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