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      Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts

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          Abstract

          We report here selective Tsuji-Trost type allylation of Ugi adducts using a strategy based on the enhanced nucleophilicity of amide dianions. Ugi adducts derived from aromatic aldehydes were easily allylated at their peptidyl position with allyl acetate in the presence of palladium catalysts. These substitutions were compared to more classical transition metal free allylations using allyl bromides.

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          Most cited references36

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          Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds.

          The sequencing of multicomponent reactions (MCRs) and subsequent cyclization reactions is a powerful stratagem for the rapid synthesis of diverse heterocyclic scaffolds. The optimal MCR is sufficiently flexible that it can be employed to generate adducts bearing a variety of functional groups that may then be selectively paired to enable different cyclization manifolds, thereby leading to a diverse collection of products. The growing interest in diversity-oriented synthesis has led to increased attention to this paradigm for library synthesis, which has inspired many advances in the design and implementation of MCRs for the construction of diverse heterocyclic scaffolds.
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            Recent Advances in Solution-PhaseMulticomponent Methodology for the Synthesis of HeterocyclicCompounds

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              Metal-mediated and metal-catalyzed reactions of isocyanides.

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                Author and article information

                Contributors
                Journal
                Front Chem
                Front Chem
                Front. Chem.
                Frontiers in Chemistry
                Frontiers Media S.A.
                2296-2646
                29 January 2019
                2019
                : 7
                : 20
                Affiliations
                [1] 1Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, ENSTA ParisTech, UMR 7652, Université Paris-Saclay , Palaiseau, France
                [2] 2Chemistry Department, Faculty of Science, Ain Shams University , Cairo, Egypt
                Author notes

                Edited by: Alexander Dömling, University of Groningen, Netherlands

                Reviewed by: Thomas J. J. Müller, Heinrich-Heine-Universität Düsseldorf, Germany; Javier Adrio, Universidad Autónoma de Madrid, Spain

                *Correspondence: Ali Khalil Ali alikhalil@ 123456sci.asu.edu.eg

                This article was submitted to Organic Chemistry, a section of the journal Frontiers in Chemistry

                Article
                10.3389/fchem.2019.00020
                6361783
                30761290
                33f6a046-1d57-4f0a-9100-79ba24ca44ad
                Copyright © 2019 Zidan, El-Naggar, Abd El-Sattar, Ali and El Kaïm.

                This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

                History
                : 30 October 2018
                : 10 January 2019
                Page count
                Figures: 7, Tables: 1, Equations: 0, References: 47, Pages: 8, Words: 3591
                Funding
                Funded by: Ministry of Scientific Research, Egypt 10.13039/501100003007
                Categories
                Chemistry
                Original Research

                ugi reaction,allylation,palladium,tsuji-trost reaction,metathesis,piperidines

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