RT info:eu-repo/semantics/article
T1 “Back‐to‐Front” Indole and Carbazole Synthesis from N,N‐Bis‐(2‐bromoallyl)amines by Combining Carbolithiation Reactions with Gold‐Catalysis
A1 Muñoz Torres, Miguel Ángel
A1 Martínez Lara, Fernando
A1 Solas Luera, Marta
A1 Suarez Pantiga, Samuel
A1 Sanz Díez, Roberto
K1 Carbolithiation
K1 Gold
K1 Homogeneous catalysis
K1 Nitrogen heterocycles
K1 Organolithiums
K1 Química analítica
K1 Chemistry, Analytic
AB The combination of organolithium chemistry with gold catalysis has enabled the development of asynthetic strategy for accessing polysubstituted indoles and carbazoles from readily available starting materials.This method is based on a “back-to-front” approach from ketopyrroles, generated by intramolecularcarbolithiation of N,N-bis-(2-lithioallyl)amines that evolve into 3,4-bis(lithiomethyl)dihydropyrrole intermediates capable of reacting with carboxylic esters and Weinreb amides. These ketopyrroles have demonstrated tobe excellent precursors of mono or bis(alkynols)pyrroles that, under gold-catalysis, experience abenzannulation reaction providing access to regioselectively substituted indoles or carbazoles.
PB Wiley
SN 1615-4150
YR 2022
FD 2022-09
LK http://hdl.handle.net/10259/7416
UL http://hdl.handle.net/10259/7416
LA eng
NO We gratefully acknowledge Ministerio de Ciencia e Innovación MCIN/AEI/10.13039/501100011033 (PID2020-115789GBC21), and Junta de Castilla y León and FEDER (BU049P20) for financial support. The project leading to these results has received funding from “la Caixa” Foundation, under the Agreement LCF/PR/PR18/51130007> (CAIXA-UBU001). M.A.M., F.M.-L., M.S. and S.S.-P. thank Junta de Castilla y León (Consejería de Educación) and Fondo Social Europeo for predoctoral (M.A.M, F.M.-L. and M.S.) and postdoctoral (S.S.- P.) contracts, respectively.
DS Repositorio Institucional de la Universidad de Burgos
RD 06-may-2024