%0 Journal Article
%A Pryyma, Alla
%A Bu, Yong Jia
%A Wai, Yonnie
%A Patrick, Brian O.
%A Perrin, David M.
%D 2019
%T Synthesis and Activation of Bench-Stable 3a-Fluoropyrroloindolines
as Latent Electrophiles for the Synthesis of C‑2-Thiol-Substituted
Tryptophans and C‑3a-Substituted Pyrroloindolines
%U https://acs.figshare.com/articles/journal_contribution/Synthesis_and_Activation_of_Bench-Stable_3a-Fluoropyrroloindolines_as_Latent_Electrophiles_for_the_Synthesis_of_C_2-Thiol-Substituted_Tryptophans_and_C_3a-Substituted_Pyrroloindolines/9959726
%R 10.1021/acs.orglett.9b02972.s001
%2 https://acs.figshare.com/ndownloader/files/17938631
%K C -3a pyrroloindolines
%K Latent Electrophiles
%K utility
%K reactivity
%K 3 a-fluoropyrroloindoline
%K COOH
%K Bench-Stable 3 a-Fluoropyrroloindolines
%K access C -2-thiol tryptophans
%K N α
%K S n 1-
%K C -3a
%K Synthesi
%X Indole dearomatization of tryptophan
represents a key approach
in the synthesis of indole containing alkaloids. Although the reactivity
of C-3a-bromo-, 3a-iodo-, and 3a-chloropyrroloindolines has
been explored, the utility and reactivity of C-3a-fluoropyrroloindolines
has remained untapped. Here we induce the C–F bond to undergo
a Sn1-like reaction. We demonstrate the utility of 3a-fluoropyrroloindoline
to access C-2-thiol-substituted tryptophans and C-3a-substituted pyrroloindolines
under mild conditions in high yield. A range of Nα-protecting groups and free -COOH are well-tolerated.
%I ACS Publications