An NMR method for assigning relative stereochemistry to beta-hydroxy ketones deriving from aldol reactions of methyl ketones |
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| Authors: | Roush William R Bannister Thomas D Wendt Michael D VanNieuwenhze Michael S Gustin Darin J Dilley Garrett J Lane Gregory C Scheidt Karl A Smith William J |
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| Institution: | Department of Chemistry, University of Michigan, Ann Arbor 48109, USA. roush@umich.edu |
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| Abstract: | We describe a simple 1H NMR analysis that permits the stereochemistry of beta-hydroxy ketones to be assigned by visual inspection of the ABX patterns for the alpha-methylene unit of the beta-hydroxy ketone in the 1H NMR spectra. This method has been verified by application to a wide range of beta-hydroxy ketones deriving from aldol reactions of chiral aldehydes with a variety of chiral and achiral methyl ketone enolates (see Tables 1 and 2). The stereochemistry of 54 of these compounds have been assigned by rigorous chemical methods. |
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