Recent Advances in Organocatalytic Asymmetric Michael Addition Reactions to α, β-Unsaturated Nitroolefins

被引:56
|
作者
Das, Tapaswini [1 ]
Mohapatra, Seetaram [1 ]
Mishra, Nilima P. [1 ]
Nayak, Sabita [1 ]
Raiguru, Bishnu P. [1 ]
机构
[1] Ravenshaw Univ, Dept Chem, Organ Synth Lab, Cuttack 753003, Odisha, India
来源
CHEMISTRYSELECT | 2021年 / 6卷 / 15期
关键词
Asymmetric Synthesis; Enantioselectivity; Hydrogen bonding; Nitroolefin; Organocatalyzed Michael addition; CONJUGATE ADDITION; BIFUNCTIONAL ORGANOCATALYSTS; RECYCLABLE ORGANOCATALYSTS; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT ORGANOCATALYSTS; CHIRAL ORGANOCATALYST; UNACTIVATED KETONES; CASCADE REACTIONS; ALDEHYDES; NITROALKENES;
D O I
10.1002/slct.202100679
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An organocatalyzed asymmetric Michael addition reaction has been established as the most relevant and dynamic research area for the construction of chiral carbon-carbon and carbon-heteroatom bond. In the current scenario, rapid revolutions on asymmetric Michael addition to nitroolefins have been explored by taking advantage of newly developed chiral organocatalysts. Moreover, nitroolefins have proven as well-known Michael acceptors for providing various structurally essential nitro-functionalized frameworks. In addition to this, remarkable stereoselectivity has been achieved in this asymmetric process by following different mechanistic pathways that involve enamine, iminium ion intermediate formation and bifunctional H-bonding interaction. So, we have discussed the recent advancements of organocatalytic Michael addition reactions to alpha, beta-unsaturated nitroolefins from the year 2016 to 2020.
引用
收藏
页码:3745 / 3781
页数:37
相关论文
共 50 条
  • [31] Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins
    Ding, Miao
    Zhou, Feng
    Qian, Zi-Qing
    Zhou, Jian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (13) : 2912 - 2914
  • [32] Recent advances in the asymmetric addition reactions of aldihydes
    Lin, CW
    Cui, JG
    Su, JY
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2000, 20 (06) : 861 - 865
  • [33] Recent Advances in Asymmetric Addition Reactions to Isatins
    Xie, Ke
    Li, Ao
    Kong, Bao-Rui
    Chen, Zhi-Chao
    Du, Wei
    Chen, Ying-Chun
    SYNTHESIS-STUTTGART, 2025, 57 (05): : 937 - 952
  • [34] Organocatalytic Enantioselective Michael Addition of Malononitrile to Nitroolefins Catalyzed by Bifunctional Thiourea
    Guo, Hai-Ming
    Li, Jian-Guo
    Qu, Gui-Rong
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    CHIRALITY, 2011, 23 (07) : 514 - 518
  • [35] Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to β,γ-Unsaturated α-Keto Esters
    Lee, Hyun Joo
    Kim, Dae Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (11): : 3537 - 3538
  • [36] Organocatalytic direct asymmetric Michael reactions of α-aminoalbehyde with β-nitroolefins:: Facile synthesis of unnatural β-disubstituted α-aminoacid.
    Thayumanavan, R
    Tanaka, F
    Barbas, CF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U548 - U548
  • [37] Asymmetric Organocatalytic Michael Addition of α,β-Unsaturated Ketone with 1,2,4-Triazole
    Zhou, Yufeng
    Li, Xin
    Li, Wenjun
    Wu, Chunlin
    Liang, Xinmiao
    Ye, Jinxing
    SYNLETT, 2010, (15) : 2357 - 2360
  • [38] A Recyclable Organocatalyst for Asymmetric Michael Addition of Acetone to Nitroolefins
    Lu, Aidang
    Liu, Tao
    Wu, Ronghua
    Wang, Youming
    Wu, Guiping
    Zhou, Zhenghong
    Fang, Jianxin
    Tang, Chuchi
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10): : 3872 - 3879
  • [39] Organocatalytic asymmetric Michael addition of pyrazoleamides to β-phthalimidonitroethene
    Luo, Yuan
    Xie, Ke-Xin
    Yue, Deng-Feng
    Zhang, Xiao-Mei
    Xu, Xiao-Ying
    Yuan, Wei-Cheng
    TETRAHEDRON, 2017, 73 (43) : 6217 - 6222
  • [40] Highly efficient asymmetric organocatalytic Michael addition of α,α-disubstituted aldehydes to nitroolefins under solvent-free conditions
    He, Junpeng
    Chen, Qiankun
    Ni, Bukuo
    TETRAHEDRON LETTERS, 2014, 55 (19) : 3030 - 3032