Stereoselective synthesis of both enantiomers of N-aryl indoles with axially chiral N-C bonds.
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.
Kamikawa
Ken
K
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan. kamikawa@c.s.osakafu-u.ac.jp
Kinoshita
Shunsuke
S
Furusyo
Masaru
M
Takemoto
Shin
S
Matsuzaka
Hiroyuki
H
Uemura
Motokazu
M
D002244:Carbon / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D017608:Chromium Compounds / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D013237:Stereoisomerism
D017608:Chromium Compounds; D007211:Indoles; D002244:Carbon; D009584:Nitrogen