Alternative strategies for the stereoselective synthesis of enantioenriched 6-arylated piperidin-2-ones

被引:11
|
作者
Sallio, Romain [1 ,2 ]
Lebrun, Stephane [1 ,2 ]
Agbossou-Niedercorn, Francine [1 ,3 ,4 ]
Michon, Christophe [1 ,3 ,4 ]
Deniau, Eric [1 ,2 ]
机构
[1] Univ Lille Nord France, F-59000 Lille, France
[2] Univ Lille 1, EA CMF 4478, Chim Organ Phys Lab, F-59655 Villeneuve Dascq, France
[3] UCCS, CNRS, UMR 8181, F-59655 Villeneuve Dascq, France
[4] ENSCL, CCM CCCF, F-59652 Villeneuve Dascq, France
关键词
HIGHLY ENANTIOSELECTIVE HYDROGENATION; ASYMMETRIC-SYNTHESIS; CATALYZED HYDROGENATION; SUZUKI-MIYAURA; PHOSPHATES; ALKALOIDS; CYCLOADDITION; COMPLEX; BOND; N; N-DIALKYLHYDRAZONES;
D O I
10.1016/j.tetasy.2012.06.024
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two alternative synthetic approaches to a variety of enantioenriched 6-arylated piperidin-2-ones have been developed. The first one is based on the hydrogenation of suitably arylated chiral cyclic enehydrazides. The second approach relies on the asymmetric catalytic hydrogenation of the corresponding N-alkylated precursors. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:998 / 1004
页数:7
相关论文
共 50 条
  • [1] An expedient stereoselective synthesis of polysubstituted piperidin-2-ones
    Barros, MT
    Januário-Charmier, MA
    Maycock, CD
    Michaud, T
    TETRAHEDRON, 2002, 58 (08) : 1519 - 1524
  • [2] Catalytic Asymmetric Allylic Alkylation of 3-Arylated Piperidin-2-ones
    Michon, Christophe
    Bethegnies, Aurelien
    Capet, Frederic
    Roussel, Pascal
    de Filippis, Arnault
    Gomez-Pardo, Domingo
    Cossy, Janine
    Agbossou-Niedercorn, Francine
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (22) : 4979 - 4985
  • [3] SYNTHESIS AND CHIROPTICAL PROPERTIES OF SOME PIPERIDIN-2-ONES
    JACKMAN, LM
    WEBB, RL
    YICK, HC
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10): : 1824 - 1831
  • [4] Intramolecular Mitsunobu reaction in the regio- and stereoselective synthesis of cis-4,5-disubstituted piperidin-2-ones
    Langlois, N
    Calvez, O
    TETRAHEDRON LETTERS, 2000, 41 (43) : 8285 - 8288
  • [5] Diastereo- and enantioselective synthesis of 4,5,6-trisubstituted and 6-monosubstituted piperidin-2-ones
    Enders, D
    Bartzen, D
    LIEBIGS ANNALEN-RECUEIL, 1997, (06): : 1115 - 1123
  • [6] Regio- and stereoselective hydroxylation of N-substituted piperidin-2-ones with Sphingomonas sp HXN-200
    Chang, DL
    Feiten, HJ
    Witholt, B
    Li, Z
    TETRAHEDRON-ASYMMETRY, 2002, 13 (19) : 2141 - 2147
  • [7] Synthesis of 3-substituted pyrrolidin-2-ones and 3-substituted piperidin-2-ones from esters
    Brunotte, Lara
    Beckmann, Lars
    Ljiljanic, Marko
    Opatz, Till
    ARKIVOC, 2024,
  • [8] Somophilic Isocyanide Insertion: Synthesis of 6-Arylated and 6-Trifluoromethylated Phenanthridines
    Wang, Ruzhi
    Jiang, Heng
    Cheng, Yuanzheng
    Kadi, Adnan A.
    Fun, Hoong-Kun
    Zhang, Yan
    Yu, Shouyun
    SYNTHESIS-STUTTGART, 2014, 46 (20): : 2711 - 2726
  • [9] Preparation and atropisomerism of 1-(2-aryl)-piperidin-2-ones
    Mörhle, H
    Jeandrée, M
    Breitmaier, E
    Rohonczy, J
    JOURNAL FUR PRAKTISCHE CHEMIE-PRACTICAL APPLICATIONS AND APPLIED CHEMISTRY, 2000, 342 (05): : 473 - 485
  • [10] Highly diastereoselective multicomponent synthesis of pyridinium-substituted piperidin-2-ones with three stereogenic centres
    Vinokurov, Andrey D.
    Iliyasov, Taygib M.
    Karpenko, Kirill A.
    Evstigneeva, Alexandra V.
    Minaeva, Alexandra P.
    Elinson, Michail N.
    Vereshchagin, Anatoly N.
    MENDELEEV COMMUNICATIONS, 2023, 33 (06) : 762 - 763