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Conformational preference in aromatic amides bearing chiral ortho substituents: its origin and application to relayed stereocontrol.

Abstract:

Tertiary aromatic amides bearing stereogenic centres ortho to the amide group may adopt two diastereoisomeric conformations which interconvert slowly on the NMR timescale at ambient temperature, and are therefore detectable by NMR. Certain classes of stereogenic centre--particularly sulfoxides, ephedrine-derived oxazolidines, and proline-derived imidazolidines--strongly bias the population of the two conformers. We propose a model, supported by molecular mechanics calculations, which rational...

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Publication status:
Published

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Publisher copy:
10.1039/b514557k

Authors


Betson, MS More by this author
Clayden, J More by this author
Helliwell, M More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MSD, Surgical Sciences
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Journal:
Organic and biomolecular chemistry
Volume:
4
Issue:
3
Pages:
424-443
Publication date:
2006-02-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:0c1b68a7-d6fd-43e4-82da-47012578f305
Source identifiers:
244886
Local pid:
pubs:244886

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