Neighboring group participation of the indole nucleus: An unusual DAST-mediated rearrangerment reaction

D.J. Hallett, U. Gerhard, S.C. Goodacre, L. Hitzel, T.J. Sparey, S. Thomas, M. Rowley, R.G. Ball

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30 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)4984-4993
Number of pages10
JournalJournal of Organic Chemistry
Volume65
Issue number16
DOIs
Publication statusPublished - 11 Aug 2000

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