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Phase-Transfer Catalysis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (15 July 2016) | Viewed by 26292

Special Issue Editors


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Guest Editor
Department of Organic Chemistry and Institute of Organic Synthesis (ISO), University of Alicante, P.O. Box 99, 03080 Alicante, Spain
Interests: metal catalysis; asymmetric catalysis; organocatalysis; materials science; medicinal chemistry; carbocatalysis; green chemistry
Special Issues, Collections and Topics in MDPI journals

E-Mail Website
Guest Editor
Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
Interests: application of organometallic compounds in organic synthesis; synthesis of heterocyclic derivatives and their application as ligands in homogeneous and heterogeneous (MOFs) catalysts
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Since the introduction of the concept "Phase Transfer Catalysis" by Starks in 1971, this methodology has played a fundamental role in organic synthesis being also widely exploited industrially. Nowadays, a wide variety of fundamental transformations can be performed under mild conditions using environmentally-friendly reagents and solvents in the presence of a catalyst (phase transfer catalyst) that facilitates the migration of a reactant from one phase into another phase where reaction takes place. Particularly interesting have resulted the advances in the development of highly active and selective phase-transfer catalysts which have converted asymmetric phase transfer catalysis in a powerful tool for the stereoselctive synthesis of a wide variety of interesting chiral compounds such as drugs and complex natural products. Also, the use of achiral phase transfer catalysts is still extensive.

This special issue will mainly focus on the latest advances and novel trends in the field of Phase-Transfer Catalysis ranging from the basic research to the development of highly active catalysts and their application for asymmetric or non-asymmetric reactions.

Dr. Diego A. Alonso
Dr. Isidro M. Pastor
Guest Editors

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • phase-transfer catalysis
  • heterogeneous catalysis
  • asymmetric catalysis
  • organocatalysis
  • cinchona alkaloids
  • ion pairing catalysis
  • green chemistry

Published Papers (3 papers)

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Research

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6484 KiB  
Article
Is Promiscuous CALB a Good Scaffold for Designing New Epoxidases?
by Isabel Bordes, José Recatalá, Katarzyna Świderek and Vicent Moliner
Molecules 2015, 20(10), 17789-17806; https://doi.org/10.3390/molecules201017789 - 25 Sep 2015
Cited by 9 | Viewed by 7264
Abstract
Candida Antarctica lipase B (CALB) is a well-known enzyme, especially because of its promiscuous activity. Due to its properties, CALB was widely used as a benchmark for designing new catalysts for important organic reactions. The active site of CALB is very similar to [...] Read more.
Candida Antarctica lipase B (CALB) is a well-known enzyme, especially because of its promiscuous activity. Due to its properties, CALB was widely used as a benchmark for designing new catalysts for important organic reactions. The active site of CALB is very similar to that of soluble epoxide hydrolase (sEH) formed by a nucleophile-histidine-acid catalytic triad and an oxyanion hole typical for molecular structures derived from processes of α/β hydrolases. In this work we are exploring these similarities and proposing a Ser105Asp variant of CALB as a new catalyst for epoxide hydrolysis. In particular, the hydrolysis of the trans-diphenylpropene oxide (t-DPPO) is studied by means of quantum cluster models mimicking the active site of both enzymes. Our results, based on semi-empirical and DFT calculations, suggest that mutant Ser105Asp CALB is a good protein scaffold to be used for the bio-synthesis of chiral compounds. Full article
(This article belongs to the Special Issue Phase-Transfer Catalysis)
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758 KiB  
Communication
Isoindolinones as Michael Donors under Phase Transfer Catalysis: Enantioselective Synthesis of Phthalimidines Containing a Tetrasubstituted Carbon Stereocenter
by Francesco Scorzelli, Antonia Di Mola, Laura Palombi and Antonio Massa
Molecules 2015, 20(5), 8484-8498; https://doi.org/10.3390/molecules20058484 - 12 May 2015
Cited by 15 | Viewed by 5888
Abstract
Readily available chiral ammonium salts derived from cinchona alkaloids have proven to be effective phase transfer catalysts in the asymmetric Michael reaction of 3-substituted isoindolinones. This protocol provides a convenient method for the construction of valuable asymmetric 3,3-disubstituted isoindolinones in high yields and [...] Read more.
Readily available chiral ammonium salts derived from cinchona alkaloids have proven to be effective phase transfer catalysts in the asymmetric Michael reaction of 3-substituted isoindolinones. This protocol provides a convenient method for the construction of valuable asymmetric 3,3-disubstituted isoindolinones in high yields and moderate to good enantioselectivity. Diastereoselectivity was also investigated in the construction of contiguous tertiary and quaternary stereocenters. The use of acrolein as Michael acceptor led to an interesting tricyclic derivative, a pyrroloisoindolinone analogue, via a tandem conjugated addition/cyclization reaction. Full article
(This article belongs to the Special Issue Phase-Transfer Catalysis)
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Review

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6875 KiB  
Review
Porphyrin-Based Metal-Organic Frameworks as Heterogeneous Catalysts in Oxidation Reactions
by Carla F. Pereira, Mário M. Q. Simões, João P. C. Tomé and Filipe A. Almeida Paz
Molecules 2016, 21(10), 1348; https://doi.org/10.3390/molecules21101348 - 12 Oct 2016
Cited by 80 | Viewed by 12320
Abstract
Porphyrin-based Metal-Organic Frameworks (Por-MOFs) constitute a special branch of the wide MOF family that has proven its own value and high potential in different applications. In this mini-review the application of these materials as catalysts in oxidation reactions is highlighted. Full article
(This article belongs to the Special Issue Phase-Transfer Catalysis)
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