Formation of All-Carbon Quaternary Centers by Copper-Catalyzed Asymmetric Conjugate Addition

Autor: Alexandre Alexakis, Magali Vuagnoux-d'Augustin, David Martin, Stefan Kehrli, Laetitia Palais, Hélène Hénon, Christine Hawner

Publikováno v: CHIMIA, Vol 62, Iss 6 (2008)

This mini-review deals with a special, and challenging, aspect of the asymmetric conjugate addition: the formation of all-carbon quaternary centers by reaction with Michael acceptors bearing a polysubstituted unsaturation. Only copper catalysts allow

Externí odkaz: https://doaj.org/article/0447e38e95ff47eca0a6351b8f63819f

Chiral NHC Ligands for the Copper-Catalyzed Asymmetric Conjugate Addition of Grignard Reagents

Autor: Magaly Magrez, Marc Mauduit, Nicolas Germain, Stefan Kehrli, Alexandre Alexakis

Publikováno v: European Journal of Organic Chemistry
European Journal of Organic Chemistry, 2012, 2012 (27), pp.5301-5306. ⟨10.1002/ejoc.201200479⟩
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
European Journal of Organic Chemistry, Wiley-VCH Verlag, 2012, 2012 (27), pp.5301-5306. ⟨10.1002/ejoc.201200479⟩
European Journal of Organic Chemistry, Vol. 2012, No 27 (2012) pp. 5301-5306

International audience; In this paper, we disclose our recent advances in the copper-catalyzed enantioselective conjugate addition of Grignard reagents to 3-substituted cyclic enones. Several new N-heterocyclic carbene (NHC) ligands have been synthes

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::53569b3fd42f62a94f93b75244e8fd97
https://hal.science/hal-00875360

Formation of quaternary chiral centers by N-heterocyclic carbene-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on trisubstituted cyclic enones

Autor: Marc Mauduit, Stefan Kehrli, Alexandre Alexakis, David C. Martin, Diane Rix

Publikováno v: Chemistry-A European Journal
Chemistry-A European Journal, Wiley-VCH Verlag, 2010, 16 (32), pp.9890-904. ⟨10.1002/chem.201000471⟩
Chemistry-A European Journal, Vol. 16, No 32 (2010) pp. 9890-9904
Chemistry-A European Journal, 2010, 16 (32), pp.9890-904. ⟨10.1002/chem.201000471⟩

International audience; The copper-catalyzed conjugate addition of Grignard reagents to 3-substituted cyclic enones allows the formation of all-carbon chiral quaternary centers. We demonstrate in this article that N-heterocyclic carbenes act as effic

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::db161d21a4e5183428b031c6d85b3d3f
https://pubmed.ncbi.nlm.nih.gov/20540048

ChemInform Abstract: Enantioselective Organocatalytic Conjugate Addition of α-Aminoketone to Nitroolefins

Autor: Stefan Kehrli, Sarah Sulzer-Mossé, Sébastien Belot, Alexandre Alexakis

Publikováno v: ChemInform. 40

The enantioselective organocatalytic conjugate addition of α-aminoketone to nitroolefins is reported.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::c8de50b25fe41aa7286856bf28a34dc4
https://doi.org/10.1002/chin.200907077

Copper-Catalyzed Asymmetric Conjugate Addition of Grignard Reagents to Trisubstituted Enones. Construction of All-Carbon Quaternary Chiral Centers

Autor: Stefan Kehrli, David C. Martin, Magali d'Augustin, Alexandre Alexakis, Hervé Clavier, Marc Mauduit

Publikováno v: Journal of the American Chemical Society
Journal of the American Chemical Society, 2006, 128 (26), pp.8416-8417. ⟨10.1021/ja0629920⟩
Journal of the American Chemical Society, Vol. 128, No 26 (2006) pp. 8416-8417
Journal of the American Chemical Society, American Chemical Society, 2006, 128 (26), pp.8416-8417. ⟨10.1021/ja0629920⟩

The copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted cyclic enones affords enantioenriched all-carbon quaternary centers with up to 96% ee. The chiral ligand is a diaminocarbene, directly generated in situ. The co

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::45d1d3b0247c638408695ff3cc98577b
https://hal.science/hal-00405350