Enantioselective Synthesis of Dihydrobenzofurans, Dihydrobenzosulfones, and Dihydroindoles by Merging One-pot Intramolecular Heck-Matsuda Reactions from Anilines with Redox-Relay Process.

Autor: Scarpa de Souza EL; Department of Organic Chemistry, University of Campinas, Rua Josué de Castro, 10384-612, Campinas, São Paulo, Brazil., Gorbatov SA; Department of Organic Chemistry, University of Campinas, Rua Josué de Castro, 10384-612, Campinas, São Paulo, Brazil., Pierozzi BM; Department of Organic Chemistry, University of Campinas, Rua Josué de Castro, 10384-612, Campinas, São Paulo, Brazil., Batista Junior JM; Institute of Science and Technology, Federal University of São Paulo, Rua Talim, 330, 12231-280, São José dos Campos, São Paulo, Brazil., Duarte Correia CR; Department of Organic Chemistry, University of Campinas, Rua Josué de Castro, 10384-612, Campinas, São Paulo, Brazil.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Aug 06; Vol. 30 (44), pp. e202401115. Date of Electronic Publication: 2024 Jul 17.
DOI: 10.1002/chem.202401115
Abstrakt: A one-pot tandem process was developed aiming at the concise and expeditious enantioselective synthesis of dihydrobenzofuran, dihydrobenzosulfone, and dihydroindole scaffolds under mild, and open-flask conditions. This process combines the in situ generation of aryldiazonium salt directly from the anilines in methanol telescoped to an intramolecular Heck-Matsuda reaction linked to a redox relay process to provide the final products as the dimethyl acetals. These Heck products were smoothly converted into the corresponding primary alcohols or esters. The robustness and the efficiency of the protocol are demonstrated by the synthesis of 24 enantioenriched dihydrobenzofurans, dihydrobenzosulfones, and dihydroindoles in overall yields up to 78 % in enantiomeric ratios up to 99 : 1 by a sequential 5-step protocol.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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