Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 14, Pages 3688-3692Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310354
Keywords
allylic amination; asymmetric catalysis; intramolecular hydroacylation; nitrogen heterocycles; rhodium
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Funding
- University of Iowa
- A. Lynn Anderson Outstanding Research Award
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Dynamic kinetic asymmetric amination of branched allylic acetimidates has been applied to the synthesis of 2-alkyl-dihydrobenzoazepin-5-ones. These seven-membered-ring aza ketones are prepared in good yield with high enantiomeric excess by rhodium-catalyzed allylic substitution with 2-amino aryl aldehydes followed by intramolecular olefin hydroacylation of the resulting alkenals. This two-step procedure is amenable to varied functionality and proves useful for the enantioselective preparation of these ring systems.
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