Commemorative Issue in Honor of Professor Pierre Vogel

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (31 August 2022) | Viewed by 10391

Special Issue Editors


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Guest Editor
Departamento de Química Física y Analítica, Laboratorio de Química Computacional, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
Interests: Complexes; Chemical structure; Carbonyls; Isomerization; Catalysts

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Guest Editor
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India
Interests: novel catalytic methodologies; synthetic organic chemistry; transition metal catalysis; visible light photocatalysis

Special Issue Information

Dear Colleagues,

Professor Pierre Vogel was born in Cully (Switzerland). He did his Ph. D under the supervision of Prof. H. Prinzbach, at the Institute of Organic Chemistry, in the University of Lausanne. He carried out post-doctoral research at Yale University (New Haven, Connecticut, USA), collaborating with Profs. M. Saunders, J.A. Berson, K.A. Wiberg and P.v.R. Schleyer (Princeton University). He then moved to Mexico City, where he worked as a Research chemist at Syntex S.A. with Prof. P. Crabbé.

In 1973, he returned to the University of Lausanne, where he became Professor of organic chemistry in 1977. In 1976, he received the Alfred Werner Medal of the Swiss Chemical Society. He was part-time doctoral schoolteacher at the Universities of Rouen and Caen from 1991 to 1993 and part-time professor at the Ecole Polytechnique in Palaiseau (France) from 1993 to 2000. He was Vice-Chairman of the Institute of Organic Chemistry at the University of Lausanne from 1991 until 2001. He was Pacific Coast (USA) Lecturer in 1992, and invited professor at the Universities of Montpellier, Paris-Sud, Ecole Supérieure de physique et de chemie industrielles de la ville de Paris (ESPCI) and Complutense (Madrid). He was awarded with the Novartis Lecturership in 2003 and was Boeringer Ingelheim Distinguished Lecturer in 2005. From 2000 to 2001, he was a reviewer of the Institut Universitaire de France, and as of 2001, Professor of organic chemistry at the Ecole Polytechnique Fédérale de Lausanne (EPFL). He also served as the Director of the doctoral program in chemistry and chemical engineering of the EPFL (2002–2010). Since 2011, he has been an Honorary Professor of the EPFL, responsible of the medicinal chemistry laboratory of the Ludwig Institute for Cancer Research, in collaboration with the EPFL. He also participates in the European FP7 health program on pancreatic cancer.

Complementing his research, Prof. Pierre Vogel has contributed more than five hundred articles in refereed journals, eleven patents, and three books.

The articles in this Special Issue represent contributions from many friends and former co-workers of Prof. Vogel who, in this way, want to show their appreciation for and friendship to Pierre.

Prof. Dr. Jose A. Sordo
Prof. Dr. Chandra M. R. Volla
Guest Editors

Manuscript Submission Information

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Keywords

  • Asymmetric total synthesis of natural products and analogues of biological interest: e.g: nonactin, polyketides, polypropionates, indolizidines, castanospermine, ryfamycin, spongistatins, apoptolidin
  • Combinatorial synthesis
  • Multicomponent synthesis
  • Furans as starting materials in fine chemistry, Biomass derived synthetic intermediates: e.g.: levoglucosenone, isolevoglucosenone
  • Glycochemistry, carbohydrates, glycomimetics, total synthesis of sugars
  • Anticancer agents, anthracyclines, iminoalditols, iminoaldoses, C-nucleosides, deoxypolyoxin-C, C-disaccharides, imino-C-disaccharides, carbasugars, conduritols, aminoconduritols, NAMPT inhibitors, ID
  • Anti-cancer vaccine candidate: C-disaccharide TF epitope analogues
  • Physical organic chemistry: e.g.: reaction mechanisms, isotopic effects, carbocations as intermediates, electron-releasing carbonyl group, barrelene effect, norbornene effects, non-planarity of pi-sys
  • Pericyclic reactions: e.g.: hetero-Diels-Alder, [4+3]-cycloaddition, cheletropic addition, dyotropic transfer of dihydrogen, Wagner-Meerwein rearrangements, sigmatropic rearrangements, ene-reactions
  • Synthesis of compounds of theoretical interest: e.g.: [l.m.n]hericenes
  • New organic chemistry of sulfur dioxide: e.g.: two-directional asymmetric synthesis of long chain polypropionates, new silylation reagents, direct amidification of carboxylic acids. Homogenous catalys
  • Transition organometallic chemistry

Published Papers (4 papers)

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Research

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15 pages, 2630 KiB  
Article
Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
by Pilar Elías-Rodríguez, Ana T. Carmona, Antonio J. Moreno-Vargas and Inmaculada Robina
Catalysts 2022, 12(8), 876; https://0-doi-org.brum.beds.ac.uk/10.3390/catal12080876 - 09 Aug 2022
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Abstract
Iminosugar derivatives containing a pyrrolidine-phosphine moiety were prepared from carbohydrates and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The corresponding 1,2,3,5-tetrasubstituted pyrrolines were obtained in good yields and diastereoselectivities but with moderate enantiocontrol. The [...] Read more.
Iminosugar derivatives containing a pyrrolidine-phosphine moiety were prepared from carbohydrates and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The corresponding 1,2,3,5-tetrasubstituted pyrrolines were obtained in good yields and diastereoselectivities but with moderate enantiocontrol. The stereochemical outcome of the reaction depends on the substituent at the nitrogen atom and hydroxyl groups, the configuration of the stereogenic centers and the distance between the diphenylphosphine group and the pyrrolidine skeleton of the catalyst. The preparation of both enantiomers of the catalyst allowed the corresponding enantiomeric pyrrolines to be obtained with similar yields, diastereo- and enantioselectivities. Full article
(This article belongs to the Special Issue Commemorative Issue in Honor of Professor Pierre Vogel)
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Review

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24 pages, 20259 KiB  
Review
Catalyzed Methods to Synthesize Pyrimidine and Related Heterocyclic Compounds
by Marcos Díaz-Fernández, Saturnino Calvo-Losada, J.-Joaquín Quirante, Francisco Sarabia, Manuel Algarra and M.-Soledad Pino-González
Catalysts 2023, 13(1), 180; https://0-doi-org.brum.beds.ac.uk/10.3390/catal13010180 - 12 Jan 2023
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Abstract
This review covers articles published in the period from 2010 to mid-2022 on synthetic advances in the formation of pyrimidine and related heterocyclic compounds. Special emphasis has been given to the different types of cycloadditions, taking into account the number of their components [...] Read more.
This review covers articles published in the period from 2010 to mid-2022 on synthetic advances in the formation of pyrimidine and related heterocyclic compounds. Special emphasis has been given to the different types of cycloadditions, taking into account the number of their components and leading to the formation of the pyrimidine ring. Due to the large number of publications on the Biginelli reaction and related reactions, this will be dealt with in a separate review in the near future. Full article
(This article belongs to the Special Issue Commemorative Issue in Honor of Professor Pierre Vogel)
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31 pages, 6494 KiB  
Review
Organic Chemistry and Synthesis Rely More and More upon Catalysts
by Pierre Vogel and Kendall N. Houk
Catalysts 2022, 12(7), 758; https://0-doi-org.brum.beds.ac.uk/10.3390/catal12070758 - 08 Jul 2022
Cited by 2 | Viewed by 2638
Abstract
A few months before the COVID-19 pandemic, Pierre Vogel and Kendall N. Houk published with a new textbook Wiley-VCH, “Organic Chemistry: Theory, Reactivity, and Mechanisms in Modern Synthesis”, with a foreword from the late Roberts H. Grubbs. The book demonstrates how [...] Read more.
A few months before the COVID-19 pandemic, Pierre Vogel and Kendall N. Houk published with a new textbook Wiley-VCH, “Organic Chemistry: Theory, Reactivity, and Mechanisms in Modern Synthesis”, with a foreword from the late Roberts H. Grubbs. The book demonstrates how catalytic processes dominate all fields of modern organic chemistry and synthesis, and how invention combines thermodynamics, kinetics, spectroscopy, quantum mechanics, and thermochemical data libraries. Here, the authors present a few case studies that should be of interest to teachers, practitioners of organic and organometallic chemistry, and the engineers of molecules. The Vogel–Houk book is both textbook and reference manual; it provides a modern way to think about chemical reactivity and a powerful toolbox to inventors of new reactions and new procedures. Full article
(This article belongs to the Special Issue Commemorative Issue in Honor of Professor Pierre Vogel)
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27 pages, 14374 KiB  
Review
Recent Advances in the Synthesis of Five-Membered Cyclic Carbonates and Carbamates from Allylic or Propargylic Substrates and CO2
by Filip Vranješević, Maria Kolympadi Markovic, Dario Matulja, Gabriela Ambrožić, José Ángel Sordo, Sylvain Laclef, Valerije Vrček and Dean Marković
Catalysts 2022, 12(5), 547; https://0-doi-org.brum.beds.ac.uk/10.3390/catal12050547 - 17 May 2022
Cited by 2 | Viewed by 2791
Abstract
The organic carbamates and carbonates are highly desirable compounds that have found a wide range of applications in drug design, medicinal chemistry, material science, and the polymer industry. The development of new catalytic carbonate and carbamate forming reactions, which employ carbon dioxide as [...] Read more.
The organic carbamates and carbonates are highly desirable compounds that have found a wide range of applications in drug design, medicinal chemistry, material science, and the polymer industry. The development of new catalytic carbonate and carbamate forming reactions, which employ carbon dioxide as a cheap, green, abundant, and easily available reagent, would thus represent an ideal substitution for existing methods. In this review, the advancements in the catalytic conversion of allylic and propargylic alcohols and amines to corresponding five-membered cyclic carbonates and carbamates are summarized. Both the metal- and the organocatalyzed methods are reviewed, as well as the proposed mechanisms and key intermediates of the illustrated carbonate and carbamate forming reactions. Full article
(This article belongs to the Special Issue Commemorative Issue in Honor of Professor Pierre Vogel)
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