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

Autor: Céline Besnard, Sébastien Goudedranche, Jérôme Lacour, Léo Egger

Publikováno v: Angewandte Chemie: International Edition, Vol. 55, No 44 (2016) pp. 13775-13779

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

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5bf0dcaea823b3f81f4b1e232ddea056
https://doi.org/10.1002/ange.201607574

Polycyclic Indoline-Benzodiazepines through Electrophilic Additions of α-Imino Carbenes to Tröger Bases

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

Publikováno v: Angewandte Chemie: International Edition, Vol. 57, No 24 (2018) pp. 7151-7155
Angewandte Chemie (International Ed. in English)

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, Fri

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::38965f646ef4def8a4959370bf1b12e3
https://archive-ouverte.unige.ch/unige:105328

Enantioselective Organocatalyzed Domino Synthesis of Six-Membered Carbocycles

Autor: Xavier Bugaut, Wilfried Raimondi, Sébastien Goudedranche, Thierry Constantieux, Damien Bonne, Jean Rodriguez

Publikováno v: Synthesis: Journal of Synthetic Organic Chemistry
Synthesis: Journal of Synthetic Organic Chemistry, 2013, 45, pp.1909-1930. ⟨10.1055/s-0033-1338484⟩
SYNTHESIS
SYNTHESIS, Georg Thieme Verlag, 2013, 45, pp.1909-1930. ⟨10.1055/s-0033-1338484⟩

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

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7fe5d0246a918252fb06a8b1ac612de9
https://doi.org/10.1055/s-0033-1338484

ChemInform Abstract: Exploiting the Reactivity of 1,2-Ketoamides: Enantioselective Synthesis of Functionalized Pyrrolidines and Pyrrolo-1,4-benzodiazepine-2,5-diones

Autor: Damien Bonne, Diana Becerra, Thierry Constantieux, Paola Acosta, Jean Rodriguez, Jairo Quiroga, Sébastien Goudedranche

Publikováno v: ChemInform. 46

A new strategy for the synthesis of optically active pyrrolo[1,4]benzodiazepine-2,5-diones has been developed. The approach is based on an initial Michael addition of functionalized 1,2-ketoamides on nitroalkenes, with a reduction–double cyclizatio

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::2f655bb5f94ab8bac42d9faf458b76e1
https://doi.org/10.1002/chin.201546058

A temporary-bridge strategy for enantioselective organocatalyzed synthesis of aza-seven-membered rings

Autor: Thierry Constantieux, Damien Bonne, Sébastien Goudedranche, Jean Rodriguez, David Pierrot

Publikováno v: Chemical Communications
Chemical Communications, Royal Society of Chemistry, 2014, 50, pp.15605-15608. ⟨10.1039/c4cc07731h⟩
Chemical Communications, 2014, 50, pp.15605-15608. ⟨10.1039/c4cc07731h⟩

International audience; We report the first enantioselective organocatalyzed domino synthesis of azepane moieties. This temporary-bridge strategy is based on a conceptually original annulation of ambident electrophilic and 1,4-bis-nucleophilic a-keto

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::94240cb9012e73af17466ef9cd19eac8
https://pubmed.ncbi.nlm.nih.gov/25360463