Enantioselective, Iridium-Catalyzed Monoallylation of Ammonia
Year: 2009
Type: article
Abstract: Highly enantioselective, iridium-catalyzed monoallylations of ammonia are reported. These reactions occur with electron-neutral, -rich, and -poor cinnamyl carbonates, alkyl and trityloxy-substituted allylic carbonates, and dienyl carbonates in moderate to good yields and excellent enantioselectivities. This process is enabled by the use of an iridium catalyst that does not require a Lewis acid for activation and that is stable toward a large excess of ammonia. This selective formation of primary allylic amines allows for one-pot syntheses of heterodiallylamines and allylic amides that are not otherwise accessible via iridium-catalyzed allylic amination without the use of blocking groups and protective group manipulations.
DOI: 10.1021/ja905059r
Authors: Mark J. Pouy, Levi M. Stanley, John F. Hartwig
Institutions: University of Illinois Urbana-Champaign, Yale University
Language: English
Subfield: Inorganic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: Amination and Etherification of Aryl Halides and Olefins, G2225206983, Mechanism and Development of Catalysts for the Synthesis of Amines, Ethers, and S, PALLADIUM CATALYZED FORMATION OF ARYLAMINE AND ARYLETHER, G734817580, Transition Metal-Catalyzed, Asymmetric Allylic Borylation and Silylation
OpenAlex ID: W2078261477