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

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-mism...

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Publication status:
Published

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Publisher copy:
10.1039/b514558a

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Institution:
University of Oxford
Department:
Oxford, MSD, Surgical Sciences
Role:
Author
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Journal:
Organic and biomolecular chemistry
Volume:
4
Issue:
3
Pages:
444-454
Publication date:
2006-02-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:fc3c166a-f1f1-4d94-889d-71a1fd46189f
Source identifiers:
244887
Local pid:
pubs:244887

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