Cascade Radical Cyclization of <i>N</i>‑Propargylindoles:
Substituents Dictate Stereoselective Formation of <i>N</i>‑Fused Indolines versus Indoles
Santosh J. Gharpure
Yogesh G. Shelke
10.1021/acs.orglett.7b02005.s001
https://acs.figshare.com/articles/journal_contribution/Cascade_Radical_Cyclization_of_i_N_i_Propargylindoles_Substituents_Dictate_Stereoselective_Formation_of_i_N_i_Fused_Indolines_versus_Indoles/5404168
An efficient protocol for the synthesis
of pyrrolo[1,2-<i>a</i>]indole derivatives having sulfide
functionality using
cascade radical cyclization on propargylindole is described. The nature
of the substituents at the propargylic carbon bearing nitrogen of
the indole has a profound effect on the rate, yield, and nature of
the product obtained by the cascade radical cyclization. An expeditious
one-pot route for cascade radical cyclization–desulfurization
is also presented. Products obtained were elaborated to the core of
the putative structure of the yuremamine and indoline derivative with
five contiguous stereocenters.
2017-09-13 17:44:39
propargylic carbon
sulfide functionality
indole
cyclization
nature
Substituents Dictate Stereoselective Formation
one-pot route
cascade Radical Cyclization