The tryptamine moiety is found in numerous biologically active natural products and pharmaceuticals. Chiral tryptamines also serve as synthetic precursor of many medicinally important indole alkaloids. As such, a direct and selective construction of chiral tryptamine derivatives from simple and readily available starting materials would provide a convenient access to a diverse indole alkaloid structural space. In this presentation, our recent chemistry development work involving a direct use of unprotected indoles and chiral sulfamidates will be discussed. The latter were easily accessible from a variety of chiral amino alcohols and provided unambiguous electrophilic location. Furthermore, the reaction conditions were carefully optimized to attain high chemoselectivity in indole alkylation (<i>N</i> vs. <i>C</i>) obviating the need for a protective group. The newly developed method proved applicable to diverse combination of indoles and sulfamidates, and its scalability has been also demonstrated.

Expedient synthesis of chiral tryptamines via a regioselective indole alkylation

256th National Meeting (2018)

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