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. Author manuscript; available in PMC: 2020 May 18.
Published in final edited form as: J Org Chem. 2018 Jun 25;83(15):7939–7949. doi: 10.1021/acs.joc.8b00812

Scheme 1.

Scheme 1.

Proposed mechanism for the synthesis of dihydroindoles from triazole 1a and rationalization of dihydroindole regioselectivity from sigmatropic rearrangements. Energetically preferred pathway shown in blue. Transition state energies are calculated relative to endo-C and are given in parenthesis as ΔG/ΔH at 343 K. See the supporting information for details. RXN = reaction, RAR = rearrangement, Rot = rotation, TS = transition state.