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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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Supplementary files

Article information


Submitted
13 Oct 2005
Accepted
23 Nov 2005
First published
22 Dec 2005

Org. Biomol. Chem., 2006,4, 444-454
Article type
Paper

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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