Enantioselective Friedel-Crafts alkylation reactions of a variety of indoles with ethyl glyoxylate, catalyzed by a chiral (S)-BINOL-Ti(IV) complex (10 mol %), are reported. The corresponding ethyl 3-indolylA C H T U N G T R E N N U N G (hydroxy)acetates were formed in good yields and with high enantiomeric excess (up to 96 %). When methyl pyruvate or p-chlorophenylglyoxal was used, the bisindole compound was obtained in excellent yield. A possible mechanism is proposed.
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The title compound, C12H12BrN2O2, is a key intermediate in the synthesis of alkaloids such as didemnimides. The crystal packing is stabilized by two intermolecular C—H...O non‐classical hydrogen bonds. In addition, there are C—H...π‐ring stacking interactions in the crystal structure.
Key indicatorsSingle-crystal X-ray study T = 298 K Mean (C-C) = 0.004 Å Disorder in main residue R factor = 0.043 wR factor = 0.110 Data-to-parameter ratio = 15.9For details of how these key indicators were automatically derived from the article, see
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