δ-Valerolactamic Quaternary Amino Acid Derivatives : Enantiodivergent Synthesis and Evidence for Stereodifferentiated β-Turn-Inducing Properties

Autor: Sandrine Py, Arnaud Martel, Sullivan Bricaud, Romain Ligny, Sopa Chewchanwuttiwong, Mathieu Y. Laurent, Rawan Hadade, Corentin Jacquemmoz, Jérôme Lhoste, Gilles Dujardin, X. M. Zhang

Publikováno v: Journal of Organic Chemistry
Journal of Organic Chemistry, American Chemical Society, 2021, 86 (12), pp.8041-8055. ⟨10.1021/acs.joc.1c00456⟩

International audience; Enantiopure (R) and (S) cyclic α,α-disubstituted amino acid derivatives displaying a δ-valerolactam side chain were prepared from a common isoxazolidine precursor. The (R)-configured δ-valerolactam 11 was converted into di

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e826de34a7c03cd5e2e67830f19b1162
https://hal.univ-grenoble-alpes.fr/hal-03371450/document

Enantioselective 1,3-Dipolar Cycloaddition Reactions of C -Carboxy Ketonitrones and Enals with MacMillan Catalysts: Evidence of a Nonconcerted Mechanism

Autor: Souhir Abid, Arnaud Martel, Mathieu Y. Laurent, Gilles Dujardin, Khalid B. Selim, Kawther Ben Ayed

Publikováno v: European Journal of Organic Chemistry. 2017:6763-6774

Highly diastereo- and enantioselective 1,3-dipolar cycloadditions between functional ketonitrones and β-substituted enals are promoted by organocatalysis with the imidazolidinium catalyst of MacMillan. Study of the scope of the reaction shows that h

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::6205133aaa842351cabe058b9979cd30
https://doi.org/10.1002/ejoc.201701307

1,3-Dipolar cycloaddition of vinyloxy quinolines with α-alkoxy carbonyl aldonitrones or cyclic surrogates: A comparative study for an asymmetric access to trans 4-quinolinoxy oxaprolines

Autor: Amany S. Mostafa, Abdelrahman Hamdi, Gilles Dujardin, Mathieu Y. Laurent, Khalid B. Selim, Mohammed A. M. Massoud, Annie Hémon-Ribaud

Publikováno v: Tetrahedron
Tetrahedron, Elsevier, 2019, 75 (3), pp.429-440. ⟨10.1016/j.tet.2018.12.019⟩

The asymmetric access to unreported trans 4-quinolinoxy oxaproline precursors is investigated here in a comparative way by 1,3-dipolar cycloaddition of vinyloxy quinolines with chiral α-alkoxycarbonyl aldonitrones and chiral cyclic surrogates.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d9aeeeaf05c636ccb35d9ed72e86d926
https://hal-univ-lemans.archives-ouvertes.fr/hal-02435143

Asymmetric Access to α-Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile

Autor: Kawther Ben Ayed, Arnaud Martel, Jean-François Poisson, Houcine Ammar, Souhir Abid, Mathieu Y. Laurent, Gilles Dujardin, Anne Beauchard, Sandrine Py

Publikováno v: European Journal of Organic Chemistry. 2014:2924-2932

Enantiopure vinyl ethers of Stericol® underwent diastereoselective thermal 1,3 dipolar cycloadditions with N-benzyl, N-benzhydryl, and N-PMB aspartate ester nitrones. Chemoselective N-debenzylation of the resulting cycloadducts afforded diastereomer

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::2a02aeea89a6577cdea51e6b21526066
https://doi.org/10.1002/ejoc.201301739

ChemInform Abstract: Synthesis of SF5-Substituted Isoxazolidines Using 1,3-Dipolar Cycloaddition Reactions of Nitrones with Pentafluorosulfanyl Acrylic Esters and Amides

Autor: Mathieu Y. Laurent, Xavier Pannecoucke, Ewelina Falkowska, Vincent Tognetti, Philippe Jubault, Laurent Joubert, Jean-Philippe Bouillon

Publikováno v: ChemInform. 47

1,3-Dipolar cycloadditions of nitrones with pentafluorosulfanyl-substituted acrylic ester and amides afforded new trisubstituted pentafluorosulfanylated isoxazolidines in moderate yields as 4-SF5-regioisomers. Theoretical calculations were carried ou

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::eae6f5b8ef512bbff2479eb2bec2d520
https://doi.org/10.1002/chin.201605150