Search

Your search keyword '"Archambeau, Alexis"' showing total 37 results
Start Over Author "Archambeau, Alexis"
37 results on '"Archambeau, Alexis"'

2. Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Straightforward Access to the (Thio)hydantoin Scaffold

Author

Busicchia, Marc, Roblin, Antoine, Dubois, Carla, Mekranter, Nagy, Casaretto, Nicolas, and Archambeau, Alexis

Abstract

A palladium-catalyzed (3 + 2) cycloaddition between 5-vinyloxazolidine-2,4-diones (VOxD) and (thio)isocyanates is described. Under optimized conditions, an array of (thio)hydantoins was readily prepared, and an enantioselective version of this transformation was then studied. To illustrate the importance of this method, a concise synthesis of two bioactive compounds, nirvanol and mephenytoin, was carried out. This work emphasizes the synthetic potential of VOxD as useful precursors of zwitterionic aza-π-allylpalladiumIIintermediates.

Published
2024
Full Text
View/download PDF

9. 1,3-Dihydroimidazolone

Author

Archambeau, Alexis and Archambeau, Alexis

Subjects
[CHIM] Chemical Sciences, [CHIM.ORGA] Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Published
2019

11. A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy Towards Oxazocine Scaffolds.

Author

Scuiller, Anaïs, Liu, Xueyang, Cordier, Marie, Garrec, Julian, and Archambeau, Alexis

Subjects
HETEROCYCLIC compounds, CARBONATES, RING formation (Chemistry), CATALYSIS
Abstract

A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation. [ABSTRACT FROM AUTHOR]

Published
2021
Full Text
View/download PDF

16. (3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Author

Cordier, Marie and Archambeau, Alexis

Abstract

Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.

Published
2024
Full Text
View/download PDF

32. Rhodium(III)-Catalyzed Allylic C(sp3)-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles.

Author

Archambeau, Alexis and Rovis, Tomislav

Subjects
*RHODIUM, *SULFONAMIDES, *CATALYSIS research, *CARBON-hydrogen bonds, *CHEMICAL research
Abstract

Unsaturated N-sulfonamides undergo a RhIII- catalyzed allylic C(sp3)H activation followed by insertion with an exogenous internal alkyne. The reaction generates [3.3.0], [4.3.0], and [5.3.0] azabicyclic structures with excellent diastereoselectivity. Deuterium labeling experiments implicate a 1,3-Rh shift as a key step in the mechanism. [ABSTRACT FROM AUTHOR]

Published
2015
Full Text
View/download PDF

33. Palladium-Catalyzed Allylic Alkylation of Allyl Dienol Carbonates: Reactivity Regioselectivity Enantioselectivity Synthetic Applications.

Author

Arseniyadis, Stellios, Fournier, J&#;r&#;my, Thangavelu, Saravanan, Lozano, Oscar, Prevost, S&#;bastien, Archambeau, Alexis, Menozzi, Candice, and Cossy, Janine

Subjects
PALLADIUM catalysts, ALLYLIC alkylation, ENOLS, CARBONATES, REGIOSELECTIVITY (Chemistry), CHEMICAL synthesis
Abstract

For the past several years, the group has focused on the development of useful synthetic tools and on executing creative and efficient routes to biologically active natural products. In this context, we recently applied the palladium-catalyzed decarboxylative allylic alkylation reaction to a new class of substrates, namely allyl dienol carbonates. This method allowed a particularly straightforward access to a wide variety of heterocycles, including 2,4-disubstituted-, 2,3,4- and 2,3,5-trisubstituted-, and 2,3,4,5- tetrasubstituted furans and pyrroles, starting from simple and readily available substrates. An asymmetric version of this method was also developed and applied to the synthesis of enantiomerically enriched butenolides and butyrolactones bearing all-carbon α- and β- quaternary stereogenic centers, respectively. This asymmetric transformation was eventually used as a key step in the total synthesis of two natural products: (-)-nephrosteranic acid and (-)-roccellaric acid. This account summarizes the results of our endeavors. 1 Introduction 2 Palladium-Catalyzed Decarboxylative Allylic Alkylation of Allyl Dienol Carbonates 2.1 Synthesis of Polysubstituted Furans 2.2 Synthesis of Polysubstituted Pyrroles 3 Asymmetric Palladium-Catalyzed Decarboxylative Allylic Alkylation of Allyl Dienol Carbonates 3.1 Synthesis of Enantiomerically Enriched Butenolides 3.2 Synthesis of Enantiomerically Enriched Furanones 3.3 Synthesis of Enantiomerically Enriched Butyrolactones 3.4 Total Syntheses of (-)-Nephrosteranic Acid and (-)-Roccellaric Acid 4 Conclusion [ABSTRACT FROM AUTHOR]

Published
2013
Full Text
View/download PDF

35. ChemInform Abstract: Rhodium(III)-Catalyzed Allylic C(sp3)-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles.

Author

Archambeau, Alexis and Rovis, Tomislav

Subjects
*CARBON-hydrogen bonds, *ELECTROCYCLIC reactions (Chemistry), *BICYCLIC compounds
Abstract

A new rhodium(III)-catalyzed allylic C(sp3)-H activation followed by 4π-electrocyclization gives access to 1-azabicycles with complete control of the formed stereocenters. [ABSTRACT FROM AUTHOR]

Published
2016
Full Text
View/download PDF

37. A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy Towards Oxazocine Scaffolds

Author

Marie Cordier, Alexis Archambeau, Anaïs Scuiller, Xueyang Liu, Julian Garrec, Laboratoire de synthèse organique (DCSO), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie moléculaire (LCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-École polytechnique (X), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), École Nationale Supérieure de Techniques Avancées (ENSTA Paris), Unité de Chimie et Procédés (UCP), Agence Nationale de la Recherche (JCJC grant CycloSyn) French National Research Agency (ANR) [ANR-18-CE07-0008], Agence Nationale de la Recherche French National Research Agency (ANR) European Commission, Labex CHARMMMAT [ANR-11-LABX-0039], ANR-18-CE07-0008,CycloSyn,Nouvelles Réactions de Cycloaddition par Catalyse Synergique(2018), ANR-11-LABX-0039,CHARMMMAT,CHimie des ARchitectures MoléculairesMultifonctionnelles et des MATériaux(2011), Archambeau, Alexis, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
heterocycles, catalysis, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Regioselectivity, chemistry.chemical_element, 010402 general chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry, 01 natural sciences, Combinatorial chemistry, Cycloaddition, 0104 chemical sciences, Catalysis, oxazocines, azadienes, Oxazocines, [CHIM] Chemical Sciences, [CHIM]Chemical Sciences, cycloaddition, Palladium, medium-sized rings
Abstract

A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

Published
2021
Full Text
View/download PDF

Catalog

Books, media, physical & digital resources
See catalog results