Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue

被引:14
作者
Sallio, Romain [1 ]
Lebrun, Stephane [1 ]
Capet, Frederic [1 ]
Agbossou-Niedercorn, Francine [1 ]
Michon, Christophe [1 ]
Deniau, Eric [1 ]
机构
[1] Univ Lille, CNRS, Cent Lille, ENSCL,Univ Artois,UMR 8181,UCCS, F-59000 Lille, France
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 14卷
关键词
asymmetric organocatalysis; Aza-Michael reaction; phase-transfer catalyst; 3-substituted isoindolinones; PHASE-TRANSFER CATALYSIS; ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; ISOINDOLIN-1-ONE DERIVATIVES; STEREOCHEMICAL CONTROL; CONJUGATE ADDITION; ORGANIC-SYNTHESIS; ACIDS; AMINATION; SOLVENT;
D O I
10.3762/bjoc.14.46
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new asymmetric organocatalyzed intramolecular aza-Michael reaction by means of both a chiral auxiliary and a catalyst for stereocontrol is reported for the synthesis of optically active isoindolinones. A selected cinchoninium salt was used as phasetransfer catalyst in combination with a chiral nucleophile, a Michael acceptor and a base to provide 3-substituted isoindolinones in good yields and diastereomeric excesses. This methodology was applied to the asymmetric synthesis of a new pazinaclone analogue which is of interest in the field of benzodiazepine-receptor agonists.
引用
收藏
页码:593 / 602
页数:10
相关论文
共 68 条
  • [1] Solvent-free double aza-Michael under ultrasound irradiation: diastereoselective sequential one-pot synthesis of pyrrolidine Lobelia alkaloids analogues
    Amara, Zacharias
    Drege, Emmanuelle
    Troufflard, Claire
    Retailleau, Pascal
    Joseph, Delphine
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (35) : 7148 - 7157
  • [2] [Anonymous], 1590565 CCDC
  • [3] Enantioselective phase-transfer-catalyzed intramolecular Aza-Michael reaction: Effective route to pyrazino-indole compounds
    Bandini, Marco
    Eichholzer, Astrid
    Tragni, Michele
    Umani-Ronchi, Achille
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (17) : 3238 - 3241
  • [4] Asymmetric Phase-Transfer-Catalyzed Intramolecular N-Alkylation of Indoles and Pyrroles: A Combined Experimental and Theoretical Investigation
    Bandini, Marco
    Bottoni, Andrea
    Eichholzer, Astrid
    Miscione, Gian Pietro
    Stenta, Marco
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (41) : 12462 - 12473
  • [5] Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium-Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates
    Barrio, Pablo
    Ibanez, Ignacio
    Herrera, Lidia
    Roman, Raquel
    Catalan, Silvia
    Fustero, Santos
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) : 11579 - 11584
  • [6] Isoindolinone enantiomers having affinity for the dopamine D4 receptor
    Belliotti, TR
    Brink, WA
    Kesten, SR
    Rubin, JR
    Wustrow, DJ
    Zoski, KT
    Whetzel, SZ
    Corbin, AE
    Pugsley, TA
    Heffner, TG
    Wise, LD
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (12) : 1499 - 1502
  • [7] Asymmetric Alkynylation/Lactamization Cascade: An Expeditious Entry to Enantiomerically Enriched Isoindolinones
    Bisai, Vishnumaya
    Suneja, Arun
    Singh, Vinod K.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (40) : 10737 - 10741
  • [8] Uncatalyzed, green aza-Michael addition of amines to dimethyl maleate
    Bosica, Giovanna
    Debono, Anthony John
    [J]. TETRAHEDRON, 2014, 70 (37) : 6607 - 6612
  • [9] Organocatalytic Aza-Michael/Retro-Aza-Michael Reaction: Pronounced Chirality Amplification in Aza-Michael Reaction and Racemization via Retro-Aza-Michael Reaction
    Cai, Yong-Feng
    Li, Li
    Luo, Meng-Xian
    Yang, Ke-Fang
    Lai, Guo-Qiao
    Jiang, Jian-Xiong
    Xu, Li-Wen
    [J]. CHIRALITY, 2011, 23 (05) : 397 - 403
  • [10] Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study
    Capobianco, Amedeo
    Di Mola, Antonia
    Intintoli, Valentina
    Massa, Antonio
    Capaccio, Vito
    Roiser, Lukas
    Waser, Mario
    Palombi, Laura
    [J]. RSC ADVANCES, 2016, 6 (38) : 31861 - 31870