Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 25, Pages 7261-7264Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602689
Keywords
aldol reactions; amides; atropisomerism; organocatalysis; stereoselectivity
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Funding
- Swiss National Science Foundation [200021-153519/1]
- Novartis AG
- Swiss National Science Foundation (SNF) [200021_153519] Funding Source: Swiss National Science Foundation (SNF)
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The increasing awareness of the importance of amide atropisomers prompts the development of novel strategies for their selective preparation. Described herein is a method for the enantioselective synthesis of atropisomeric aromatic amides by an amine-catalyzed arene-forming aldol condensation. The high reactivity of the glyoxylic amide substrates enables a remarkably efficient construction of a new aromatic ring, which proceeds within minutes at ambient temperature to afford products with excellent stereoselectivity. The high rotational barriers of the reduced products highlight the utility of this stable, spatially organized chiral scaffold.
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