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Synfacts 2006(9): 0912-0912  
DOI: 10.1055/s-2006-942060
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Diastereoselective Intermolecular C-H Amination

Contributor(s): Mark Lautens, Yann Béthuel
C. Liang, F. Robert-Peillard, C. Fruit, P. Müller*, R. H. Dodd*, P. Dauban*
University of Geneva, Switzerland and , Institut de Chimie des Substances Naturelles, Gif sur Yvette, France
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Over the last few years, metal-catalyzed C-H functionalization has been an area of intense research. In particular, intramolecular amination reactions of saturated C-H bonds represented a powerful tool for the synthesis of chiral nitrogen-containing compounds (for recent examples, see: J.-S. Liang et al. J. Org. Chem. 2004, 69, 3610-3619; M. Kim et al. Org. Lett. 2006, 8, 1073-1076). Herein the first efficient intermolecular version of this reaction is described, using catalytic amounts of chiral rhodium complex[Rh2{(S)-nttl}4], substoichiometric amounts of alkane and a combination of PhI(OCOt-Bu)2 and (S)-N-(p-toluenesulfonyl)-p-toluenesulfonimid­amide to afford the chiral iminoiodane in situ.