Electrophilic carbonyl activation: competing condensative cyclizations of tryptamine derivatives
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Movassaghi_Electrophilic carbonyl.pdf
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3.5 MB
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Author(s)
Liu, Fan
Movassaghi, Mohammad
Date Issued
September 2014
Journal
Tetrahedron Letters
Publisher
Elsevier
Citation
Liu, Fan, and Mohammad Movassaghi. “Electrophilic Carbonyl Activation: Competing Condensative Cyclizations of Tryptamine Derivatives.” Tetrahedron Letters 56, no. 23 (June 2015): 2995–3000.
Version
Author's final manuscript
Abstract
A series of tryptamine derived bisindole substrates were subjected to electrophilic activation of the func-tional grouping at their [alpha]-nitrogen in the form of iminium ions to enable cyclization onto the sterically hindered indole substructure. Our observations regarding divergent cyclization outcomes using electronically distinct bisindole substrates are described. Surprising preference for the Friedel–Crafts alkylation reaction and evidence for an intriguing reversible spirocyclization are discussed.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-NonCommercial-NoDerivs License
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DOI of Published Version
https://doi.org/10.1016/j.tetlet.2014.09.022
