Gold(I)-catalyzed divergent and diastereoselective synthesis of azepines by ammoniumation/ring-expansion reactions

Autor: Patrick Pale, Romain Pertschi, Aurélien Blanc, Jean-Marc Weibel, Nicolas Kern, Solène Miaskiewicz

Publikováno v: Chem Catalysis
Chem Catalysis, Elsevier, 2021, 1 (1), pp.129-145. ⟨10.1016/j.checat.2021.02.004⟩

Summary Gold(I) catalysts enable the chemoselective addition of tailor-made N-sulfonylated azetidine derivatives onto alkynes, affording bicyclic vinyl-ammonium gold intermediates. Intramolecularly intercepted by an adequately positioned nucleophilic

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5a6e92cc3ff5258b78578a120e16240c
https://doi.org/10.1016/j.checat.2021.02.004

Stereoselective Synthesis of C,C-Glycosides from exo-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer

Autor: Philippe Compain, Damien Tardieu, Marine Desnoyers, Claire Laye, Damien Hazelard, Nicolas Kern

Publikováno v: Organic Letters
Organic Letters, American Chemical Society, 2019, 21 (18), pp.7262-7267. ⟨10.1021/acs.orglett.9b02496⟩

We describe herein a convenient strategy for the construction of C,C-glycoside building blocks via the intermediacy of tertiary pseudoanomeric radicals. Application of an iron-mediated hydrogen atom transfer/Michael-Giese coupling enables the anomeri

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d6b40a3a2455ccaf2b0a8a3b5cb373c1
https://doi.org/10.1021/acs.orglett.9b02496

Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams

Autor: Solène Miaskiewicz, Anne-Sophie Felten, Nicolas Kern, Aurélien Blanc, Patrick Pale, Jean-Marc Weibel, Fatih Sirindil, Arno Lalaut

Publikováno v: Tetrahedron. 73:5096-5106

2-Carboxylated aza-rings have been synthesized in two steps through a highly selective monohalogenation of N -sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogena

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::7b8f50469e13216d4f6173a54a384ab3
https://doi.org/10.1016/j.tet.2017.06.067

Gold(I)-Catalyzed N-Desulfonylative Amination versus N-to-O 1,5-Sulfonyl Migration: A Versatile Approach to 1-Azabicycloalkanes

Autor: Aurélien Blanc, Solène Miaskiewicz, Jean-Marc Weibel, Patrick Pale, Nicolas Kern, Boris Gaillard

Publikováno v: Angewandte Chemie International Edition. 55:9088-9092

Valuable 1-azabicycloalkane derivatives have been synthesized through a novel gold(I)-catalyzed desulfonylative cyclization strategy. An ammoniumation reaction of ynones substituted at the 1-position with an N-sulfonyl azacycle took place in the pres

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9da0771883b4c09628f7b285990e3d99
https://doi.org/10.1002/anie.201604329

Enantioselective cyclizations and cyclization cascades of samarium ketyl radicals

Autor: Nicolas Kern, Mateusz P. Plesniak, David J. Procter, Joseph J. W. McDouall

Publikováno v: Kern, N, Plesniak, M, Mcdouall, J & Procter, D 2017, ' Enantioselective cyclizations and cyclization cascades of samarium ketyl radicals ', Nature Chemistry, vol. 9, pp. 1198-1204 . https://doi.org/10.1038/nchem.2841

The rapid generation of molecular complexity from simple starting materials is a key challenge in synthetic science. Enantioselective radical cyclization cascades have the potential to deliver complex, densely-packed, polycyclic architectures, with c

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::10015d2df5e8680d7545d1a283237ad6
https://pubmed.ncbi.nlm.nih.gov/29168498