Organic Letters
Organic Letters
5 years ago

Enantiospecific Synthesis of β-Substituted Tryptamines

Enantiospecific Synthesis of β-Substituted Tryptamines
Heather N. Rubin, Jennifer Cockrell, Kinney Van Hecke, Jeremy B. Morgan, Jonathan J. Mills
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02474

DOI: 10.1021/acs.orglett.7b02474

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