Enantioselective, iridium-catalyzed monoallylation of ammonia.
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.
Pouy
Mark J
MJ
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.
Stanley
Levi M
LM
Hartwig
John F
JF
D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D000641:Ammonia / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000498:Allyl Compounds; D000588:Amines; D002254:Carbonates; D007495:Iridium; D000641:Ammonia