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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Iridium-catalyzed C3-selective asymmetric allylation of 7-azaindoles with secondary allylic alcohols
Takahiro Sawano1, Takeshi Matsui1, Marina Koga1
1Department of Chemistry and Biological Science, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan. takeuchi@chem.aoyama.ac.jp.
Abstract:
The development of efficient synthetic methods of 7-azaindoles has been desired due to the useful biological activities and physical properties. We report the first example of the iridium-catalyzed C3-selective asymmetric allylation of 7-azaindoles with racemic secondary allylic alcohols to give only branched allylation products in good to high yields with high enantioselectivity (up to >99.5% ee). Allylic alcohols and 7-azaindoles with a variety of functional groups including halogen and heteroaromatic groups are compatible with the reaction conditions. Furthermore, transformations of the obtained allylation products are demonstrated without a significant loss of enantiomeric excess.
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