Enantiospecific Synthesis of β‑Substituted Tryptamines
journal contributionposted on 07.09.2017, 14:18 by Heather N. Rubin, Kinney Van Hecke, Jonathan J. Mills, Jennifer Cockrell, Jeremy B. Morgan
Any type of content formally published in an academic journal, usually following a peer-review process.
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.