This work investigates the synthetic utility of <i>N</i>-tosyl 2-alkenylaniline oxides. Under acidic conditions the epoxide undergoes a transannulation-elimination sequence that affords an indole containing compound. However, when the epoxide is treated with certain nucleophiles, intramolecular N-H activation can provide regioselective control affording several interesting products including 1,2-aminoalcohols. The variety of products that can be prepared will be demonstrated.

Synthesis of indole derivatives and 1,2-aminoalcohols via <i>N</i>-tosyl 2-alkenylaniline oxides

253rd National Meeting (2017)

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Synthesis of indole derivatives and 1,2-aminoalcohols via N-tosyl 2-alkenylaniline oxides