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Your search keyword '"Morwenna S. M. Pearson-Long"' showing total 6 results
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6 results on '"Morwenna S. M. Pearson-Long"'

1. Titanium-Mediated Addition of Grignard Reagents to Acyl Cyanohydrins: Aminocyclopropane versus 1,4-Diketone Formation

Author

Gwénaël Forcher, Philippe Bertus, Fabien Boeda, Paul Setzer, and Morwenna S. M. Pearson-Long

Subjects
Diketone, 010405 organic chemistry, Organic Chemistry, Grignard reaction, 010402 general chemistry, 01 natural sciences, 3. Good health, 0104 chemical sciences, Cyclopropane, chemistry.chemical_compound, chemistry, Reagent, Moiety, Organic chemistry, Reactivity (chemistry), Physical and Theoretical Chemistry, Titanium isopropoxide, Tetrahydrofuran
Abstract

The 1,2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples), giving both aminocyclopropane derivatives and 1,4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1,4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), the cyclopropane derivatives were obtained in good yields. The observed dichotomy may be explained by a ring-opening of the five-membered titanacycle intermediate followed by a nonselective acyl addition.

Published
2013

2. Titanium-Mediated Synthesis of 1,4-Diketones from Grignard Reagents and Acyl Cyanohydrins

Author

Morwenna S. M. Pearson-Long, Alice Beauseigneur, Paul Setzer, Philippe Bertus, Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and ANR-07-BLAN-0283,SAAcoude,Aminoacides à conformation contrôlée: Nouvelles approches stéréosélectives et application à la conception de librairies de coudes beta(2007)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, chemistry.chemical_element, General Medicine, General Chemistry, 010402 general chemistry, carbonyl compound, 01 natural sciences, Catalysis, grignard reagents, 3. Good health, 0104 chemical sciences, chemistry.chemical_compound, metallacycles, Reagent, synthetic methods, Organic chemistry, titanium, ComputingMilieux_MISCELLANEOUS, Cyanohydrin, Titanium
Abstract

The cyanohydrin substrates react with titanacyclopropanes, obtained in situ from Grignard reagents and Ti(OiPr)4, to produce 1,4-diketones.

Published
2010

3. Titanium-Catalyzed Cyclopropanation of Boc-Protected Cyanohydrins: A Short Access to Aminocyclopropanecarboxylic Acid Derivatives

Author

Jan Szymoniak, Alice Beauseigneur, Philippe Bertus, Philippe Karoyan, Morwenna S. M. Pearson-Long, Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Synthèse, Structure et Fonction de Molécules Bioactives (SSFMB), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Reims Champagne-Ardenne (URCA)-Centre National de la Recherche Scientifique (CNRS)-SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Centre National de la Recherche Scientifique (CNRS), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, amino acids, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Chemistry, Cyclopropanation, Organic Chemistry, technology, industry, and agriculture, chemistry.chemical_element, Catalysis, organometallic reagents, Amino acid, Cyclopropane, chemistry.chemical_compound, cyclopropane, Organic chemistry, cyanohydrins, titanium, ComputingMilieux_MISCELLANEOUS, Titanium
Abstract

The preparation of protected 1-aminocyclopropanecarboxylic acid was performed from readily available and inexpensive start-ing materials, using titanium-catalyzed cyclopropanation as the key step. As an extension of this methodology, a diastereoselective synthesis of the cis-2-vinyl-substituted analogue is presented.

Published
2010

4. ChemInform Abstract: Titanium-Mediated Addition of Grignard Reagents to Acyl Cyanohydrins: Aminocyclopropane versus 1,4-Diketone Formation

Author

Philippe Bertus, Gwénaël Forcher, Fabien Boeda, Morwenna S. M. Pearson-Long, and Paul Setzer

Subjects
Diketone, chemistry.chemical_compound, chemistry, Reagent, Moiety, Reactivity (chemistry), General Medicine, Titanium isopropoxide, Diethyl ether, Medicinal chemistry, Tetrahydrofuran, Cyclopropane
Abstract

The 1,2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples), giving both aminocyclopropane derivatives and 1,4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1,4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), the cyclopropane derivatives were obtained in good yields. The observed dichotomy may be explained by a ring-opening of the five-membered titanacycle intermediate followed by a nonselective acyl addition.

Published
2014

5. Simple and convenient access to α,α,α-trisubstituted amides by double addition of Grignard reagents to acyl cyanohydrins

Author

Souhir Abid, Philippe Bertus, Paul Setzer, Fatma Boukattaya, Houcine Ammar, Morwenna S. M. Pearson-Long, Andrii Stanovych, Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS), Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Faculté des Sciences de Sfax, Université de Sfax - University of Sfax, Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), and Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
chemistry.chemical_classification, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Aryl, Metals and Alloys, Nucleophilic acyl substitution, General Chemistry, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, 3. Good health, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, chemistry.chemical_compound, Reagent, Materials Chemistry, Ceramics and Composites, Organic chemistry, [CHIM]Chemical Sciences, lipids (amino acids, peptides, and proteins), Alkyl, ComputingMilieux_MISCELLANEOUS
Abstract

The double addition of Grignard (alkyl, aryl, alkenyl, alkynyl) reagents to acyl cyanohydrins was performed under unusually smooth conditions with a concomitant O–N acyl transfer, providing a very simple and general access to α,α,α-trisubstituted amides.

Published
2012

6. ChemInform Abstract: Titanium-Mediated Synthesis of 1,4-Diketones from Grignard Reagents and Acyl Cyanohydrins

Author

Paul Setzer, Morwenna S. M. Pearson-Long, Alice Beauseigneur, and Philippe Bertus

Subjects
chemistry.chemical_compound, Chemistry, Reagent, Organic chemistry, chemistry.chemical_element, General Medicine, Cyanohydrin, Titanium
Abstract

The cyanohydrin substrates react with titanacyclopropanes, obtained in situ from Grignard reagents and Ti(OiPr)4, to produce 1,4-diketones.

Published
2011

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