Diastereoselective Synthesis of Highly Functionalized γ-Lactams via Ugi Reaction/Michael Addition

被引:0
|
作者
机构
[1] Vidal, Herika D. A.
[2] Nunes, Paulo S. G.
[3] Martinez, Alice K. A.
[4] Januário, Marcelo A. P.
[5] Santiago, Pedro H. O.
[6] Ellena, Javier
[7] Corrêa, Arlene G.
基金
巴西圣保罗研究基金会;
关键词
Carbonyl compounds - Stereoselectivity;
D O I
10.1002/asia.202400917
中图分类号
学科分类号
摘要
The γ-lactam ring is a prominent feature in medicinal chemistry, and its synthesis has garnered significant interest due to its valuable properties. Among the γ-lactams, 2-oxopyrrolidine-3-carbonitrile derivatives stand out as versatile synthons that can be readily transformed into a variety of other functional groups. In this work, we successfully synthesized highly functionalized 3-cyano-2-pyrrolidinones with moderate to good overall yields using the Ugi reaction followed by intramolecular Michael addition. The process demonstrated excellent diastereoselectivity and showed good tolerance to a range of isonitriles and carbonyl compounds. © 2024 Wiley-VCH GmbH.
引用
收藏
相关论文
共 50 条
  • [31] Highly efficient diastereoselective Michael addition of various thiols to (+)-brefeldin A
    Argade, AB
    Haugwitz, RD
    Devraj, R
    Kozlowski, J
    Fanwick, PE
    Cushman, M
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02): : 273 - 278
  • [32] A solvent-free synthesis of highly functionalized benzothiazolediamides (mimic natural peptide) via Ugi four component reaction
    Farahani, Fatemeh Sheikholeslami
    Shahvelayati, Ashraf S.
    AMINO ACIDS, 2011, 41 : S78 - S78
  • [33] Synthesis of Highly Functionalized Proline Derivatives via a One-Pot Michael/SN′-Addition/Cyclization Approach
    Kazmaier, Uli
    Schmidt, Christian
    SYNTHESIS-STUTTGART, 2009, (14): : 2435 - 2439
  • [34] Highly Diastereoselective Synthesis of Multifunctionalized Dihydrofurans by a K3PO4-Promoted Michael Addition-Alkylation Reaction
    Feng, Juhua
    Feng, Jinxiang
    Li, Juanhong
    Huang, Ailin
    Hu, Haipeng
    Yang, Shengnan
    Liu, Kuan
    Yue, Guizhou
    CHEMISTRYSELECT, 2023, 8 (37):
  • [35] Highly Diastereoselective Synthesis of γ-Lactams Enabled by Photoinduced Deaminative [3+2] Annulation Reaction
    Shi, Chengcheng
    Guo, Lin
    Gao, Han
    Luo, Mengqi
    Yang, Chao
    Xia, Wujiong
    ORGANIC LETTERS, 2022, 24 (24) : 4365 - 4370
  • [36] Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions
    Popik, Oskar
    Grzeszczyk, Barbara
    Staszewska-Krajewska, Olga
    Furman, Bartlomiej
    Chmielewski, Marek
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (15) : 2852 - 2860
  • [37] Organocatalytic Enantioselective Cascade Aza-Michael/Michael Addition for the Synthesis of Highly Functionalized Tetrahydroquinolines and Tetrahydrochromanoquinolines
    Yang, Wen
    He, Hai-Xiao
    Gao, Yu
    Du, Da-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3670 - 3678
  • [38] An efficient synthesis of highly functionalized chiral lactams
    Ornelas, Martha A.
    Gonzalez, Javier
    Sach, Neal W.
    Richardson, Paul F.
    Bunker, Kevin D.
    Linton, Angelica
    Kephart, Susan E.
    Pairish, Mason
    Guo, Chuangxing
    TETRAHEDRON LETTERS, 2011, 52 (37) : 4760 - 4763
  • [39] Diastereoselective Synthesis of Bicyclo[3.2.1]octanes via Catalyst-Free Cascade Michael/Henry Reaction with a Functionalized Vinylogous Nucleophile
    An, Laiyu
    Chen, Linghong
    Yang, Hongzhou
    Ye, Ling
    Yang, Hongjun
    Li, Xinying
    Zhao, Zhigang
    Li, Xuefeng
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (17) : 2969 - 2975
  • [40] Synthesis of functionalized cyclohexenols via a domino Michael addition-Dieckmann cyclization-isomerization reaction sequence
    Bakthadoss, Manickam
    Murugan, Gandhi
    Srinivasan, Jayakumar
    TETRAHEDRON LETTERS, 2015, 56 (25) : 3877 - 3881