Allènylmétaux

Les allényl–propargyl métaux constituent une famille de réactifs plurifonctionnels offrant une grande panoplie de possibilités synthétiques. La préparation de ces composés et l’étude de leur réactivité constitue l’une des thématiques de référence de l’équipe. Parmi les problématiques abordées, nous nous sommes par exemple intéressés aux allénylsilanes chiraux ou encore à la condensation d’allénylzincs ou allénylcuivres avec des tert-butanesulfinylimines. Cette combinaison s’est avérée un mariage très fécond et nous a permis de développer de nombreuses applications en synthèse totale.

  • Stereoselective Synthesis of 4-Hydroxy-1-Silyl-1-Allenylboranes and Access to 2-Silylethynyl-1,3-Diols. El Haj Brahim, I.; Ishak Dridi, I.; Abderrahim, R.; Fabrice Chemla, F.; Ferreira, F.; Jackowski, O.; Pérez-LunaA.;  Asian J. Org. Chem. 2024, e202400042, accepted; https://doi.org/10.1002/ajoc.202400042
  • β‐Amino Propargylic Fluorides through Stereoselective Electrophilic Fluorodesilylation of 4‐Amino‐1‐allenylsilanes. Bochatay, V. N.; Chemla, F.; Ferreira, F.; Jackowski, O.; Pérez-Luna, A. Eur. J. Org. Chem. 2018, 3862 ; http://dx.doi.org/10.1002/ejoc.201800862.
  • Synthesis of allenylzinc reagents by 1,2-rearrangement of alkynyl(disilyl)zincates derived from acetylenic epoxides and acetylenic aziridines. Bochatay, V. N.; Debien, L.; Chemla, F.; Ferreira, F.; Jackowski, O.; Perez-Luna, A. C. R. Chim. 2017, 20, 609–616 ; http://dx.doi.org/10.1016/j.crci.2017.02.001.
  • Ring-Opening of N-Tert-Butanesulfinylethynylaziridines with Lithium Tris(dimethylphenylsilyl)zincate: Stereoselective Access to 4-Amino-1-Allenylsilanes. Bochatay, V. N.; Sanogo, Y.; Chemla, F.; Ferreira, F.; Jackowski, O.; Pérez-Luna, A. Adv. Synth. Catal. 2015, 357, 2809–2814 ; http://dx.doi.org/10.1002/adsc.201500347.
  • Three-Carbon Homologation of Diorganozincs with Lithiated Acetylenic Epoxides. Denichoux, A.; Debien, L.; Cyklinsky, M.; Kaci, M.; Chemla, F.; Ferreira, F.; Perez-Luna, A. J. Org. Chem. 2013, 78, 134–145 ; http://dx.doi.org/10.1021/jo302128n.
  • Metallotropic Equilibrium and Configurational Stability of 3-Chloro-1-(Trimethylsilyl)propargyl and -Allenyl Metals: Comparative Study among Lithium, Titanium, and Zinc. Bejjani, J.; Botuha, C.; Chemla, F.; Ferreira, F.; Magnus, S.; Pérez-Luna, A. Organometallics 2012, 31, 4876–4885 ; http://dx.doi.org/10.1021/om300420q.
  • Stereoselective Synthesis of syn-β-Amino Propargylic Ethers. Application to the Asymmetric Syntheses of (+)-ß-Conhydrine and (–)-Balanol. Louvel, J.; Chemla, F.; Demont, E.; Ferreira, F.; Pérez-Luna, A.; Voituriez, A. Adv. Synth. Cat. 2011, 353, 2137–2151. DOI: 10.1002/adsc.201100333
  • Diastereoselective Synthesis of Homopropargylic N-tert-Butylsulfinylamines. Cyclinsky, M.; Botuha, C.; Chemla, F.; Ferreira, F.; Pérez-Luna, A. Synlett 2011, 2681–2684. DOI:10.1021/ol202747p
  • Synthesis of of (–)-Swainsonine and (–)-8-epi-Swainsonine by the Addition of Allenylmetals to Chiral α,ß-Alkoxy Sulfinylimines. Louvel, J.; Chemla, F.; Demont, E.; Ferreira, F.; Pérez-Luna, A. Org. Lett. 2011, 13, 6452–6455. DOI: 10.1021/ol202747p
  • Asymmetric total synthesis of (+)-6-epi-castanospermine through stereoselective formation of a syn,anti acetylenic 2-amino-1,3-diol stereotriad. Louvel, J.; Botuha, C.; Chemla, F.; Ferreira, F.; Pérez-Luna, A.; Demont, E. Eur. J. Org. Chem. 2010, 2921–2926. DOI: 10.1002/ejoc.201000202
  • Stereo- and Enantioselective Synthesis of Acetylenic 2-Amino-1,3-Diol Stereotriads. Voituriez, A.; Pérez-Luna, A.; Ferreira, F.; Botuha C.; Chemla, F. Org. Lett. 2009, 11, 931–934. DOI: 10.1021/ol802912f
  • Expeditious Synthesis of a Common Intermediate of L-1-Deoxyallonojirimycin and L-1-Deoxymannojirimycin. Ferreira, F.; Botuha C.; Chemla, F.; Pérez-Luna, A. J. Org. Chem. 2009, 74, 2238–2241. DOI: 10.1021/jo802757f
  • Concise Synthesis of (2S,3R)-3-Hydroxy-2-phenylpipezridine: An Advanced Key Intermediate of Human Non-Peptide NK-1 Receptor Antagonists. Hélal, B.; Ferreira, F.; Botuha C.; Chemla, F.; Pérez-Luna, A. Synlett 2009, 3115–3118. DOI: 10.1055/s-0029-1218308
  • High-Yielding Synthesis of Sphingoid-Type Bases. Séguin, C.; Ferreira, F.; Botuha C.; Chemla, F.; Pérez-Luna, A. J. Org. Chem. 2009, 74, 6986–6992. DOI: 10.1021/jo901567q
  • Addition of a 3-alkoxy allenylzinc to N-acyliminium ions: new entry to propargyl syn-1,2-aminoalcohol units. Roy, B; Pérez-Luna, A.; Ferreira, F.; Botuha, C.; Chemla, F. Tetrahedron Lett. 2008, 49, 1534–1537. DOI:10.1016/j.tetlet.2007.12.102
  • Stereoselective Synthesis of Enantioenriched Acetylenic 1,2-Amino Alcohols. Chemla, F.; Ferreira, F.; Gaucher, X.; Palais, L. Synthesis 2007, 1235–1241. DOI: 10.1055/s-2007-965989
  • Short and Efficient Asymetric Synthesis of (-)-ß-Conhydrine. Voituriez, A.; Ferreira, F.; Chemla, F. J. Org. Chem. 2007, 72, 5358–5361. https://doi.org/10.1021/jo070760t
  • Asymmetric Synthesis of (–)-1-Hydroxyquinolizidinone, a Common Intermediate for the Syntheses of (–)-Homopumiliotoxin 223G and (–)-Epiquinamide. Voituriez, A.; Ferreira, F.; Perez-Luna, A.; Chemla, F. Org. Lett. 2007, 9, 4705–4708. DOI: 10.1021/ol701952y