Gold-ringing! Modification of the substitution at C2 drives an entirely different cyclization of N-tethered allenylindoles. An efficient cycloisomerization takes place for the case of R being hydrogen, that is, compatible with additional functional groups. A methyl at C2 precludes this possibility and launches a stepwise process that can be tuned to yield macrocyclic trimers.
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Barluenga et al. (2010) studied this question.
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