An NMR method for assigning relative stereochemistry to β-hydroxy ketones deriving from aldol reactions of methyl ketones

William R. Roush*, Thomas D. Bannister, Michael D. Wendt, Michael S. VanNieuwenhze, Darin J. Gustin, Garrett J. Dilley, Gregory C. Lane, Karl A. Scheidt, William J. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

We describe a simple 1H NMR analysis that permits the stereochemistry of β-hydroxy ketones to be assigned by visual inspection of the ABX patterns for the α-methylene unit of the β-hydroxy ketone in the 1H NMR spectra. This method has been verified by application to a wide range of β-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.

Original languageEnglish (US)
Pages (from-to)4284-4289
Number of pages6
JournalJournal of Organic Chemistry
Volume67
Issue number12
DOIs
StatePublished - Jun 14 2002

ASJC Scopus subject areas

  • Organic Chemistry

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