Enantioselective Synthesis of 1,2 and 1,3-diamines and Development of multicomponent reactions in oxidative conditions

The aim of this study is the development of new access to highly functionalized nitrogen-containing compounds with respect to the green chemistry principles.First, an Ugi four-component reaction from alcohols has been studied. In the presence of hypervalent iodine compounds, used as oxidant and introduced in stoechiometric or catalytic quantites, an efficient one-pot sequence has been developed.Then, a new four-component Mannich reaction using a catalytic amount of BINOL-derived phosphoric acid gave an access to enantioenriched 1,3-diamines from enamides. Changing the electrophilic imine partner to a diazene compound afforded aminoketones or 1,2-diamines precursors in high yields and excellent enantiomeric excess.Finally, two new iron-catalyzed multicomponent reactions of enamides with TEMPO and various nucleophiles provided an efficient synthesis of aminoalcohols derivatives. These domino reactions involving an oxidative process from enamides offered a convenient and economical method to establish two C-O bonds in a single operation.

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Source https://theses.hal.science/tel-00823407
Author Drouet, Fleur
Maintainer CCSD
Last Updated May 11, 2026, 02:51 (UTC)
Created May 11, 2026, 02:51 (UTC)
Identifier NNT: 2011PA112344
Language fr
Rights https://about.hal.science/hal-authorisation-v1/
contributor Institut de Chimie des Substances Naturelles (ICSN) ; Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)
creator Drouet, Fleur
date 2011-12-16T00:00:00
harvest_object_id dbce7210-3243-4cde-937e-6811c931cdeb
harvest_source_id 3374d638-d20b-4672-ba96-a23232d55657
harvest_source_title test moissonnage SELUNE
metadata_modified 2026-04-13T00:00:00
set_spec type:THESE