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Enantiospecific Synthesis of β‑Substituted Tryptamines

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journal contribution
posted on 07.09.2017, 14:18 by Heather N. Rubin, Kinney Van Hecke, Jonathan J. Mills, Jennifer Cockrell, Jeremy B. Morgan
Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis where isomer formation can be controlled. 3,5-Dinitrobenzoyl (DNB)-protected aziridines undergo regioselective, enantiospecific ring opening to produce β-substituted tryptamines for a series of indoles. Attack at the more substituted aziridine carbon occurs in an SN2-like fashion to generate DNB-tryptamine products as synthetic precursors.