Synfacts 2008(6): 0603-0603  
DOI: 10.1055/s-2008-1072625
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Heterobimetallic Catalyst for Intermolecular C-H Amination

Contributor(s): Hisashi Yamamoto, Marina Naodovic
S. A. Reed, M. C. White*
University of Illinois, Urbana, USA
Further Information

Publication History

Publication Date:
21 May 2008 (online)

Significance

In the previous report, White demonstrated the power of Pd/sulfoxide catalyst 1 on the direct intramolecular C-H amination (K. J. Fraunhoffer, M. C. White J. Am. Chem. Soc. 2007, 129, 7274.) This latest report from White’s group shows that a more difficult intermolecular alternative is feasible using the Pd/sulfoxide-Cr(salen) couple. Remarkably, the reaction is carried out in a highly regio- and diastereoselective fashion. The outstanding feature of this method is the possibility of accessing the nitrogen functionality in unactivated olefins circumventing an oxygenated precursor.