Download PDF
Synfacts 2007(10): 1069-1069  
DOI: 10.1055/s-2007-969008
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Hydroamination of N-Allenyl Carbamates via Gold(I)

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
Z. Zhang, C. F. Bender, R. A. Widenhoefer*
Duke University, Durham, USA
Further Information

Publication History

Publication Date:
07 November 2007 (online)

    Permissions and Reprints

Significance

In connection with previous work on the enantioselective, intramolecular hydroxyalkoxylation and hydroarylation of allenes catalyzed by chiral gold complexes (Angew. Chem. Int. Ed. 2007, 46, 283 and Org. Lett. 2007, 9, 1935) the authors report the enantioselective hydroamination of N-allenyl carbamates using a bis(gold)-phosphine complex. Notably, a wide array of carb­amate and carboxamide nucleophiles are tolerated giving high yields and ee values. While disubstituted allenes give consistently high enantioselectivities, their unsubstituted counterparts do not.