1627156-71-1Relevant articles and documents
Rhodium-catalyzed sequential allylic amination and olefin hydroacylation reactions: Enantioselective synthesis of seven-membered nitrogen heterocycles
Arnold, Jeffrey S.,Mwenda, Edward T.,Nguyen, Hien M.
supporting information, p. 3688 - 3692 (2014/04/17)
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. A two-step process has been developed for the formation of enantioenriched seven-membered-ring aza ketones under mild conditions. The approach consists of a rhodium-catalyzed asymmetric amination of allylic trichloroacetimidates with 2-aminobenzaldehydes (C-N bond) followed by intramolecular hydroacylation (C-C bond) of the alkenal products and exhibits broad substrate scope and functional-group tolerance (see example).
