Stereoselective synthesis of both enantiomers of N-aryl indoles with axially chiral N-C bonds |
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Authors: | Kamikawa Ken Kinoshita Shunsuke Furusyo Masaru Takemoto Shin Matsuzaka Hiroyuki Uemura Motokazu |
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Affiliation: | Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan. kamikawa@c.s.osakafu-u.ac.jp |
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Abstract: | N-Aryl indoles with axially chiral N-C bonds were synthesized by stereoselective nucleophilic aromatic substitution reactions of planar chiral tricarbonyl(2,6-disubstituted-1-fluorobenzene)chromium complexes. The stereochemistry of the products is highly dependent on the position of the substituent in the indole. When indoles devoid of a substituent at the 2-position were used, N-aryl indole chromium complexes having anti orientation with respect to the tricarbonylchromium fragment were obtained diastereoselectively. In contrast, 2-substituted indoles gave the N-aryl indoles with syn orientation between the tricarbonylchromium fragment and the benzene ring of the indole. These results demonstrate that we have succeeded in synthesizing both enantiomers of N-aryl indoles utilizing an identical planar chiral arene chromium complex. |
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