297165-79-8Relevant academic research and scientific papers
Neighboring group participation of the indole nucleus: An unusual DAST-mediated rearrangerment reaction
Hallett, David J.,Gerhard, Ute,Goodacre, Simon C.,Hitzel, Laure,Sparey, Timothy J.,Thomas, Steven,Rowley, Michael,Ball, Richard G.
, p. 4984 - 4993 (2000)
A rearrangement reaction involving the indole nucleus was investigated using stereochemical markers and low-temperature NMR experiments. Treatment of(3S,4S)-3-hydroxy-4-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with diethylaminosulfur trifluoride gave stereospecifically (3S,4S)-4-fluoro-3-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with complete regioselectivity. The initial formation of a reactive spirocyclopropyl-3H-indole intermediate is believed to be responsible for the stereo- and regiochemical outcome of the reaction.
