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.
来源：
Corrêa, Arlene G. (agcorrea@ufscar.br) | 2025年 / 20卷 / 01期
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
  • [41] Asymmetric Michael-Michael addition of aminoester to nitroalkene: Synthesis of polycyclic lactams
    Gautam, Lekh Nath Sharma
    Yan, Wuming
    Shi, Xiaodong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [42] Diastereoselective formation of β-lactams via a three-component reaction
    Shao, Ying
    Tian, Shijie
    Zhu, Jie
    Tang, Shengbiao
    Sun, Jiangtao
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (21) : 9989 - 9993
  • [43] Highly diastereoselective synthesis of a novel functionalized triepoxytrinaphthylene
    Erdogan, Musa
    Essiz, Selcuk
    Fabris, Fabrizio
    Dastan, Arif
    ARKIVOC, 2018, : 134 - 143
  • [44] Diastereoselective Synthesis of Highly Functionalized Proline Derivatives
    Philippova, Anna N.
    Vorobyeva, Daria V.
    Gribanov, Pavel S.
    Dolgushin, Fedor M.
    Osipov, Sergey N.
    MOLECULES, 2022, 27 (20):
  • [45] Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones
    Baumann, Marcus
    Baxendale, Ian R.
    SYNTHESIS-STUTTGART, 2018, 50 (04): : 753 - 759
  • [46] Convergent diastereoselective synthesis of isopilocarpine by one-pot Michael-addition-alkylation reaction
    Braun, M
    Bühne, C
    Cougali, D
    Schaper, K
    Frank, W
    SYNTHESIS-STUTTGART, 2004, (17): : 2905 - 2909
  • [47] Liquid-phase combinatorial synthesis of alicyclic β-lactams via Ugi four-component reaction
    Gedey, S
    Van der Eycken, J
    Fulöp, F
    ORGANIC LETTERS, 2002, 4 (11) : 1967 - 1969
  • [48] Ultrasound-assisted diastereoselective green synthesis of spiro-fused-γ-lactams functionalized with an amide bond heterocyclic bioisostere via the Ugi azide/domino process coupled strategy
    Calderon-Rangel, David
    Renteria-Gomez, Angel
    Cruz-Jimenez, Alicia E.
    Gomez, Manuel A. Renteria
    Jimenez-Halla, J. Oscar C.
    Gamez-Montano, Rocio
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (26) : 5289 - 5295
  • [49] Synthesis of Highly Functionalized Proline Derivatives via a One-pot Michael/Aldol Addition-Cyclization Approach
    Kazmaier, Uli
    Schmidt, Christian
    SYNLETT, 2009, (07) : 1136 - 1140
  • [50] Highly diastereoselective synthesis of modified nucleosides via an asymmetric multicomponent reaction
    Ghosh, Arun K.
    Kass, Jorden
    CHEMICAL COMMUNICATIONS, 2010, 46 (08) : 1218 - 1220
12345