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Your search keyword '"Sébastien Goudedranche"' showing total 8 results
Start Over Author "Sébastien Goudedranche" Topic 010405 organic chemistry
8 results on '"Sébastien Goudedranche"'

1. Expeditious Synthesis of Enantioenriched Tetrahydropyrans via Chemoselective C−N bond Cleavage of Aza-Oxa-Bicyclo[3.2.1]Octanes

Author

Damien Bonne, Jean Rodriguez, Sébastien Goudedranche, Thierry Constantieux, Cecilia Sasso D'Elia, Marco Bella, Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), Dipartimento di Chimica, Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome], Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome] (UNIROMA)

Subjects
Bicyclic molecule, Organocatalysis, Oxocarbenium ions, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, Oxocarbenium, Azepanes, Multiple bond-forming transformations, Tetrahydropyrans, Organo- catalysis, General Chemistry, Tetrahydropyran, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, chemistry.chemical_compound, Electrophile, Enantiomeric excess, Bond cleavage, Octane
Abstract

International audience; A rapid synthesis of enantioenriched 2,3,4-trisubstituted tetrahydropyrans in good yields and stereoselectivities is reported. The first step is a domino organocatalytic reaction between ambident electrophilic and 1,4-bis-nucleophilic 1,2-ketoamides and 1,3-bis-electrophilic enals, leading to aza-oxa-bicyclo[3.2.1]octane. Then, the TiCl4/Et3SiH system ensures a chemoselective cleavage of the C−N bond and affords the desired trisubstituted tetrahydropyran in good yield and with conservation of the precursors optical purity. This final synthetic operation includes two consecutive oxocarbenium ion formation and reductions.

Published
2017
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2. Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams

Author

Céline Besnard, Sébastien Goudedranche, Jérôme Lacour, and Léo Egger

Subjects
010405 organic chemistry, Aryl, General Chemistry, General Medicine, 010402 general chemistry, 01 natural sciences, Catalysis, Pyrrolidine, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Yield (chemistry), Reagent, Pyrrolizidine, ddc:540, Structural isomer, Organic chemistry, Diazo, Lewis acids and bases
Abstract

N-aryl γ-lactams react intermolecularly with acceptor–acceptor diazo reagents, usually dicarbonyl compounds, in a copper-catalyzed process to yield functionalized pyrrolidines with α-pseudoquaternary centers. As 1,2-acyl or -phosphoryl migration is preferred, single regioisomers are obtained. Furthermore, in the presence of a Lewis acid, subsequent Friedel–Crafts reactions yield tricyclic pyrrolizidines in excellent yields (90–96 %) and diastereoselectivities (up to >20:1).

Published
2016
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3. Polycyclic Indoline-Benzodiazepines through Electrophilic Additions of α-Imino Carbenes to Tröger Bases

Author

Alessandro Bosmani, Alejandro Guarnieri-Ibáñez, Céline Besnard, Jérôme Lacour, and Sébastien Goudedranche

Subjects
Models, Molecular, Indoles, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Medicinal chemistry, Catalysis, Stereocenter, chemistry.chemical_compound, Benzodiazepines, Polycyclic Compounds, 010405 organic chemistry, Chemistry, indolines, Communication, Stereoisomerism, General Medicine, General Chemistry, Triazoles, cascade reactions, Communications, 3. Good health, 0104 chemical sciences, Homogeneous Catalysis, Yield (chemistry), Indoline, Electrophile, rhodium, α-imino carbenes, ddc:540, Aminal, Imines, Carbene, Methane
Abstract

Polycyclic indoline‐benzodiazepines can be accessed through the intermolecular reaction of Tröger bases with N‐sulfonyl‐1,2,3‐triazoles. Under RhII catalysis, α‐imino carbenes are generated and a subsequent cascade of [1,2]‐Stevens, Friedel–Crafts, Grob, and aminal formation reactions yield the polycyclic heterocycles as single isomers (d.r.>49:1, four stereocenters including two bridgehead N atoms). Further ring expansion by insertion of a second α‐imino carbene leads to elaborated polycyclic 9‐membered‐ring triazonanes.

Published
2018

4. α,β-Unsaturated Acyl Cyanides as New Bis-Electrophiles for Enantioselective Organocatalyzed Formal [3+3]Spiroannulation

Author

Xavier Bugaut, Sébastien Goudedranche, Jean Rodriguez, Thierry Constantieux, Damien Bonne, Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), ANR-11-BS07-0014,OEREKA,Réactions Enantiosélectives Organocatalysées à partir de Cétoamides(2011), and Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Stereochemistry, Chemistry, domino reactions, Organic Chemistry, spiroannulation, Enantioselective synthesis, General Chemistry, Optically active, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Catalysis, Domino, 0104 chemical sciences, Acylation, Organocatalysis, enantioselectivity, Electrophile, organocatalysis, Reactivity (chemistry), glutarimides
Abstract

International audience; α,β-Unsaturated acyl cyanides are key bis-electrophile substrates for successful domino enantioselective organocatalyzed Michael-intramolecular acylation domino sequences. This new reactivity has been applied to the synthesis of enantioenriched azaspiro[4,5]decanone ring systems by a formal [3+3]spiroannulation, constituting a rare example of synthesis of glutarimides in an optically active form.

Published
2013
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5. Enantioselective Organocatalyzed Domino Synthesis of Six-Membered Carbocycles

Author

Xavier Bugaut, Wilfried Raimondi, Sébastien Goudedranche, Thierry Constantieux, Damien Bonne, Jean Rodriguez, Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), STeRéO, Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), and Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)

Subjects
multicomponent reactions, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Cyclohexenes, domino reactions, asymmetric synthesis, Organic Chemistry, Enantioselective synthesis, 010402 general chemistry, 01 natural sciences, Catalysis, Domino, 0104 chemical sciences, Stereocenter, chemistry.chemical_compound, chemistry, Organocatalysis, Organic chemistry, organocatalysis, cyclohexenes, Organic synthesis, cyclohexanes
Abstract

Polysubstituted chiral cyclohexanes and cyclohexenes are important building blocks in organic synthesis. From historical and pioneering reports to the most recent accounts, this review focuses on domino enantioselective organocatalytic methodologies that have allowed the control of the relative and absolute configurations of up to six stereogenic centers in the construction of these versatile molecular architectures. 1 Introduction 2 Two-Component Transformations 2.1 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds 2.2 Michael-Initiated Domino Reactions with Nitroolefins 2.3 Non Michael-Initiated Domino Reactions 3 Multicomponent and Related Transformations 3.1 Pseudo-Three-Component Reactions 3.1.1 Michael-Initiated Domino Reactions with Nitroolefins 3.1.2 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds 3.2 Consecutive Reactions 3.2.1 Michael-Initiated Domino Reactions with Nitroolefins 3.2.2 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds 3.3 Multicomponent Reactions 3.3.1 Michael-Initiated Domino Reactions with Nitroolefins 3.3.2 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds 4 Conclusion

Published
2013
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6. Organocatalytic Multicomponent Reactions of 1,3-Dicarbonyls for the Synthesis of Enantioenriched Heterocycles

Author

Jean Rodriguez, Xavier Bugaut, Haiying Du, Sébastien Goudedranche, Thierry Constantieux, Yohan Dudognon, Maria del Mar Sanchez Duque, Damien Bonne, Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), ANR-07-CP2D-0006,CIL-MCRS,Reactions Domino Multicomposés et Liquides Ioniques à Tâches Spécifiques : Nouvelles Approches Eco-Compatibles en Synthèse Organique(2007), ANR-11-BS07-0014,OEREKA,Réactions Enantiosélectives Organocatalysées à partir de Cétoamides(2011), and Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
heterocycles, 010405 organic chemistry, Chemistry, multicomponent reactions, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Enantioselective synthesis, 3-dicarbonyls, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, Michael addition, enantioselectivity, organocatalysis
Abstract

In this feature article, a general perspective of the research program aimed towards the preparation of polycyclic heterocycles by the means of enantioselective organocatalytic multicomponent reactions is presented. Guidelines for reaction design, including the selection of substrates and organocatalysts are discussed. For all transformations, scope and limitations are presented, along with post-functionalization to afford diversified heterocyclic scaffolds. 1 Introduction 2 Type I Products: 1,4,5,6-Tetrahydropyridines 3 Type II Products: 1,2,3,4-Tetrahydropyridines 4 Type III Products: Bridged Perhydropyridines 5 Conclusion and Perspective

Published
2016
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7. Activation of 1,2- and 1,3-Ketoamides with Thiourea Organocatalyst for the Enantioselective Domino Synthesis of Fuctionalized Cyclohexanes

Author

Xavier Bugaut, Wilfried Raimondi, Maria del Mar Sanchez Duque, Adrien Quintard, Jean Rodriguez, Sébastien Goudedranche, Damien Bonne, Thierry Constantieux, STeRéO, Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), and Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)

Subjects
Bicyclic molecule, ketones, catalysis, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, domino reactions, cyclizations, Enantioselective synthesis, cycloalkanes, 010402 general chemistry, stereoselectivity, 01 natural sciences, Combinatorial chemistry, Domino, 0104 chemical sciences, Stereocenter, amides, chemistry.chemical_compound, Thiourea, chemistry, Cyclohexanes, thioureas, Bifunctional, Chirality (chemistry)
Abstract

International audience; Several reactive sites of 1,2- and 1,3-ketoamides were successively exploited in two complementary domino transformations for the synthesis of polysubstituted monocyclic or bridged bicyclic cyclohexanes, with the creation of up to six stereogenic centers. In both cases, a chiral bifunctional thiourea organocatalyst allowed efficient control of chirality in the final carbocycle.

Published
2013
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8. The shortest synthetic route to puromycin analogues using a modified robins approach

Author

Peter Strazewski, Denis Bouchu, Kollappillil S. Krishnakumar, Sébastien Goudedranche, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-École Supérieure Chimie Physique Électronique de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Depierre, Frédérique

Subjects
Magnetic Resonance Spectroscopy, medicine.drug_class, Stereochemistry, Carboxamide, 010402 general chemistry, 01 natural sciences, Chemical synthesis, chemistry.chemical_compound, Structure-Activity Relationship, Deoxyadenosine, medicine, Deoxyadenosines, Molecular Structure, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Stereoisomerism, [CHIM.ORGA] Chemical Sciences/Organic chemistry, Isocyanate, 0104 chemical sciences, chemistry, Puromycin, One pot reaction, Yield (chemistry), Indicators and Reagents, Derivative (chemistry)
Abstract

International audience; We are reporting on the utility of commercial vinyl isocyanate for a practical synthetic route from adenosine to N(6)-bis-demethylpuromycin in seven steps and 65% overall yield. A clean one-pot conversion of 3'-bromo-2'-carbamoyl derivative 8 to 3'-amino-3'-deoxyadenosine derivative 10 is the main feature of this synthetic pathway. This synthesis is the shortest synthetic route toward 3'-(aminoacylamido)deoxyadenosines to date.

Published
2011

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