- 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...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1039/b514558a
-
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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
- Copyright date:
- 2006
Journal article
Conformational arm-wrestling: battles for stereochemical control in benzamides bearing matched and mismatched chiral 2- and 6-substituents.
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