%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