8
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: found
      • Article: found
      Is Open Access

      Non-Covalent Organocatalyzed Domino Reactions Involving Oxindoles: Recent Advances

      review-article

      Read this article at

      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          The ubiquitous presence of spirooxindole architectures with several functionalities and stereogenic centers in bioactive molecules has been appealing for the development of novel methodologies seeking their preparation in high yields and selectivities. Expansion and refinement in the field of asymmetric organocatalysis have made possible the development of straightforward strategies that address these two requisites. In this review, we illustrate the current state-of-the-art in the field of spirooxindole synthesis through the use of non-covalent organocatalysis. We aim to provide a concise overview of very recent methods that allow to the isolation of unique, densely and diversified spirocyclic oxindole derivatives with high structural diversity via the use of cascade, tandem and domino processes.

          Related collections

          Most cited references59

          • Record: found
          • Abstract: found
          • Article: not found

          Organocatalytic cascade reactions as a new tool in total synthesis.

          The total synthesis of natural products and biologically active compounds, such as pharmaceuticals and agrochemicals, has reached an extraordinary level of sophistication. We are, however, still far away from the 'ideal synthesis' and the state of the art is still frequently hampered by lengthy protecting-group strategies and costly purification procedures derived from the step-by-step protocols. In recent years several new criteria have been brought forward to solve these problems and to improve total synthesis: atom, step and redox economy or protecting-group-free synthesis. Over the past decade the research area of organocatalysis has rapidly grown to become a third pillar of asymmetric catalysis standing next to metal and biocatalysis, thus paving the way for a new and powerful strategy that can help to address these issues - organocatalytic cascade reactions. In this Review we present the first applications of such asymmetric organocascade reactions to the total synthesis of natural products.
            Bookmark
            • Record: found
            • Abstract: not found
            • Article: not found

            Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products

              Bookmark
              • Record: found
              • Abstract: found
              • Article: not found

              Chiral squaramide derivatives are excellent hydrogen bond donor catalysts.

              Thioureas represent the dominant platform for hydrogen bond promoted asymmetric catalysts. A large number of reactions, reported in scores of publications, have been successfully promoted by chiral thioureas. The present paper reports the use of squaramides as a highly effective new scaffold for the development of chiral hydrogen bond donor catalysts. Squaramide catalysts are very simple to prepare. The (-)-cinchonine modified squaramide (5), easily prepared through a two-step process from methyl squarate, was shown to be an effective catalyst, even at catalyst loadings as low as 0.1 mol%, for the conjugate addition reactions of 1,3-dicarbonyl compounds to beta-nitrostyrenes. The addition products were obtained in high yields and excellent enantioselectivities.
                Bookmark

                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                MDPI
                1420-3049
                29 September 2017
                October 2017
                : 22
                : 10
                : 1636
                Affiliations
                [1 ]Dipartimento di Scienze, Sezione di Nanoscienze e Nanotecnologie, Università degli Studi Roma Tre, via della Vasca Navale 79, I-00146 Roma, Italy; martina.miceli@ 123456icloud.com
                [2 ]ICGM-Institut Charles Gerhardt Montpellier, UMR 5253 CNRS-UM-ENSCM, Ecole Nationale Supérieure de Chimie, 8, Rue de l’Ecole Normale, 34296 Montpellier CEDEX 5, France; jean-marc.campagne@ 123456enscm.fr
                Author notes
                [* ]Correspondence: tecla.gasperi@ 123456uniroma3.it (T.G.); renata.marcia_de_figueiredo@ 123456enscm.fr (R.M.d.F.); Tel.: +39-06-5733-3371 (T.G.); +33-467-147-224 (R.M.d.F.)
                Author information
                https://orcid.org/0000-0003-3638-2517
                https://orcid.org/0000-0001-7058-672X
                https://orcid.org/0000-0002-4943-047X
                https://orcid.org/0000-0001-5336-6071
                Article
                molecules-22-01636
                10.3390/molecules22101636
                6151767
                28961217
                2496f2e9-1695-4039-b5fb-581b3116031e
                © 2017 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 16 September 2017
                : 26 September 2017
                Categories
                Review

                spirooxindole derivatives,non-covalent organocatalysis,hydrogen-bonding,cascade,tandem,domino,enantioselectivity,chiral building blocks

                Comments

                Comment on this article