Fabien Gagosz

University of Ottawa

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Florin M. Istrate

Laboratoire de Synthèse Organique

Yann Odabachian

École Polytechnique Fédérale de Lausanne

Shunsuke Chiba

Nanyang Technological University

Andrea K. Buzas

University of Geneva

Samir Z. Zard

Centre National de la Recherche Scientifique

Dominic Campeau

University of Ottawa

X.F. Le Goff

Centre National de la Recherche Scientifique

Dhika Aditya Gandamana

Nanyang Technological University

Guilhem Henrion

École Polytechnique

Ciputra Tejo

Nanyang Technological University

Cooperative Institutions

Centre National de la Recherche Scientifique

École Polytechnique

Laboratoire de Synthèse Organique

Chinese Academy of Sciences

University of Ottawa

Nanyang Technological University

Heteroelements and Coordination Chemistry Lab

Kunming Institute of Botany

University of Chinese Academy of Sciences

Aarhus University

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Au-Catalyzed Formation of Functionalized Quinolines from 2-Alkynyl Arylazide Derivatives

Organic Letters (2013)

Colombe Gronnier Guillaume Boissonnat Fabien Gagosz

A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.

Functional group

Reaction conditions

Sequence (biology)

10.1021/ol4019634

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Citations (109)

Hydroalkylation of Alkynyl Ethers via a Gold(I)-Catalyzed 1,5-Hydride Shift/Cyclization Sequence

Journal of the American Chemical Society (2010)

Igor D. Jurberg Yann Odabachian Fabien Gagosz

A series of alkynyl ethers react with an electrophilic gold(I) catalyst to produce a range of structurally complex spiro or fused dihydrofurans and dihydropyrans via a 1,5-hydride shift/cyclization sequence. This hydroalkylation process, which is performed under practical experimental conditions, can be applied to terminal as well as ester-substituted alkynes. It allows the efficient conversion of secondary or tertiary sp3 C−H bonds into new C−C bonds by the nucleophilic addition of a vinylgold species onto an oxonium intermediate. The stereoselectivity of the cycloisomerization process toward the formation of a new five- or six-membered cycle appears to be dependent on steric factors and the alkyne substitution pattern.

Oxonium ion

Alkyne

Cycloisomerization

Nucleophilic Addition

Catalytic cycle

10.1021/ja9100134

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Citations (154)

Stereoselective Formation of Functionalized 2,5-Dihydrofurans

Synfacts (2006)

Fabien Gagosz A. BUZAS Florin M. Istrate

Optically active starting materials are smoothly converted into the corresponding 2,5-dihydrofurans with high levels of chirality transfer. Primary, secondary, and tertiary alcohol groups gave high yields in all cases. For the reaction using chiral starting materials, only the primary alcohols did not show high chirality transfer. The reaction proceeds through an allenyl intermediate which is cyclized by the gold(I) catalyst to generate the product.

Chirality

Tertiary alcohols

Primary (astronomy)

10.1055/s-2006-941918

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CCDC 811771: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

Stephanie N. Kramer Y. Odabachin Jacob Overgaard Mario Rottländer Fabien Gagosz

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccw7q5z

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CCDC 1894805: Experimental Crystal Structure Determination

The Cambridge Structural Database (2019)

Bin Wang Dhika Aditya Gandamana Fabien Gagosz Shunsuke Chiba

10.5517/ccdc.csd.cc21lpr3

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CCDC 1503988: Experimental Crystal Structure Determination

The Cambridge Structural Database (2016)

Geoffroy Hervé Lonca Ciputra Tejo Hui Ling Chan Shunsuke Chiba Fabien Gagosz

10.5517/ccdc.csd.cc1mh0rw

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CCDC 2069301: Experimental Crystal Structure Determination

The Cambridge Structural Database (2021)

Min Jin Congyun Tang Yingying Li Shuai Yang Ying-Tao Yang

10.5517/ccdc.csd.cc27g8nn

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Acyl Fluorides as Efficient Electrophiles for the Copper-Catalyzed Boroacylation of Allenes

ACS Catalysis (2017)

Arnaud Boreux Kiran Indukuri Fabien Gagosz Olivier Riant

The copper-catalyzed reaction of allenes with bis(pinacolato)diboron and acyl electrophiles is reported. In this transformation, acyl fluorides have been proven to be more efficient coupling partners than their chloride or carboxylate analogues. The optimized reaction conditions employed were shown to be compatible with a range of commonly used functional groups, thereby allowing the formation of a library of β-boryl β,γ-unsaturated ketones by varying the nature of the allene and acyl fluoride substrates.

Allene

Carboxylate

Acyl chloride

10.1021/acscatal.7b02938

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Citations (113)

ChemInform Abstract: Au‐Catalyzed Formation of Functionalized Quinolines from 2‐Alkynyl Arylazide Derivatives.

ChemInform (2013)

Colombe Gronnier Guillaume Boissonnat Fabien Gagosz

Abstract A novel gold‐catalyzed method to convert 2‐alkynyl arylazides into polysubstituted quinolines is developed.

10.1002/chin.201402157

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Generation and Capture of Iminyl Radicals from Ketoxime Xanthates

Synlett (1999)

Fabien Gagosz Samir Z. Zard

Irradiation of ketoxime O-(S-methyl xanthates) containing a γ,δ-double bond leads to a dihydropyrrole through cyclisation of an intermediate iminyl radical in a radical chain reaction. The last propagation step involves transfer of a dithiocarbonate group and various external radical traps can be incorporated into the medium, allowing access to a variety of substituted dihydropyrroles.

Free-radical reaction

10.1055/s-1999-2971

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Citations (46)