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Enantioselective, iridium-catalyzed monoallylation of ammonia.

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.

SUBMITTER: Pouy MJ

PROVIDER: S-EPMC2746482 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Enantioselective, iridium-catalyzed monoallylation of ammonia.

Pouy Mark J MJ Stanley Levi M LM Hartwig John F JF

Journal of the American Chemical Society 20090801 32

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 ...[more]

PMID: 19722644

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