Synfacts 2006(5): 0466-0466  
DOI: 10.1055/s-2006-934353
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Formation of Axially Chiral N-Aryl Indoles and Stereoselective Functionalization

Contributor(s): Mark Lautens, Frédéric Ménard
K. Kamikawa*, S. Kinoshita, H. Matsuzaka, M. Uemura*
Kyoto Pharmaceutical University, Japan
Further Information

Publication History

Publication Date:
21 April 2006 (online)

Significance

Using planar chiral arene chromium complexes, the stereoselective synthesis of axially chiral N-aryl indoles by a nucleophilic substitution reaction was achieved. Stereoselective Cr(CO)3 migration to the arene ring of the indole occurred by refluxing 4 in toluene to give a single diastereo­mer. The migration proceeds in an intramolecular fashion and the 1,3-dioxolane group (R3) is crucial for this reaction. Further chemo- and stereoselective transformation to control the chirality at the side chain is possible utilizing the planar chiral indole fragment. The stereochemical integrity of Cr-free N-aryl indoles 3 or 4 is stable to heating.