Tryptamines are important organic small molecules for the treatment of human disease. Beta-substituted tryptamines are less prevalent in natural systems, hence the study of possible biomedical applications requires new synthetic organic methodology. Enantioenriched <i>N</i>-acylaziridines undergo stereocontrolled ring opening in the presence of indole and a Lewis acid to produce tryptamines with unique substitution patterns. Specifically, beta-substituted tryptamine derivatives are produced in one step with good yields as a single enantiomer. The reaction details and efforts towards a catalytic, enantioselective process will be disclosed.

Synthesis of enantioenriched β-substituted tryptamine derivatives

251st National Meeting (2016)

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