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Issue 3, 2006
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Conformational arm-wrestling: battles for stereochemical control in benzamides bearing matched and mismatched chiral 2- and 6-substituents

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Abstract

The orientation of a tertiary amide group adjacent to an aromatic ring may be governed by the stereochemistry of an adjacent chiral substituent. With a chiral substituent in both ortho positions, matched/mismatched pairs of isomers result. Evidence for matched stereochemistry is provided by the clean NMR spectra of single conformers, while mismatching gives poor or unexpected selectivities in the formation of chiral substituents, or mixtures of amide conformers. Attempts to use the match–mismatch effect to select for racemic pairs of enantiomeric substituents, and hence develop a “racemate-sequestering” reagent, are described, along with the use of “matching” to scavenge a single enantiomer of a diamine from material of incomplete enantiomeric purity.

Graphical abstract: Conformational arm-wrestling: battles for stereochemical control in benzamides bearing matched and mismatched chiral 2- and 6-substituents

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Publication details

The article was received on 13 Oct 2005, accepted on 23 Nov 2005 and first published on 22 Dec 2005


Article type: Paper
DOI: 10.1039/B514558A
Citation: Org. Biomol. Chem., 2006,4, 444-454
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    Conformational arm-wrestling: battles for stereochemical control in benzamides bearing matched and mismatched chiral 2- and 6-substituents

    J. Clayden, Y. J. Y. Foricher, M. Helliwell, P. Johnson, D. Mitjans and V. Vinader, Org. Biomol. Chem., 2006, 4, 444
    DOI: 10.1039/B514558A

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