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
  • [21] Organocatalytic and direct asymmetric vinylogous Michael addition of α,α-dicyanoolefins to α,β-unsaturated aldehydes
    Xie, JW
    Yue, L
    Xue, D
    Ma, XL
    Chen, YC
    Wu, Y
    Zhu, J
    Deng, JG
    CHEMICAL COMMUNICATIONS, 2006, (14) : 1563 - 1565
  • [22] Recent advances of organocatalytic enantioselective Michael-addition to chalcone
    Sabita Nayak
    Subhendu Chakroborty
    Sujitlal Bhakta
    Pravati Panda
    Seetaram Mohapatra
    Research on Chemical Intermediates, 2016, 42 : 2731 - 2747
  • [23] Recent advances of organocatalytic enantioselective Michael-addition to chalcone
    Nayak, Sabita
    Chakroborty, Subhendu
    Bhakta, Sujitlal
    Panda, Pravati
    Mohapatra, Seetaram
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (04) : 2731 - 2747
  • [24] Organocatalytic asymmetric Michael addition of α-aryl cyclopentanones to nitroolefins for construction of adjacent quaternary and tertiary stereocenters
    Dong, Xiu-Qin
    Teng, Huai-Long
    Tong, Min-Chao
    Huang, He
    Tao, Hai-Yan
    Wang, Chun-Jiang
    CHEMICAL COMMUNICATIONS, 2010, 46 (36) : 6840 - 6842
  • [25] Organocatalytic Asymmetric Michael Addition of 4-Hydroxycoumarin to β,γ-Unsaturated α-Keto Esters
    Suh, Chang Won
    Han, Tae Hyun
    Kim, Dae Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (06): : 1623 - 1624
  • [26] Recent Advances in Organocatalyzed Asymmetric sulfa-Michael Addition Triggered Cascade Reactions
    Niu, Cheng
    Du, Da-Ming
    CHEMICAL RECORD, 2023, 23 (07):
  • [27] Recent Advances in Catalytic Asymmetric Aza-Michael Addition Triggered Cascade Reactions
    Song, Yong-Xing
    Du, Da-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (20) : 4667 - 4694
  • [28] Highly efficient organocatalytic asymmetric Michael addition of homoserine lactone derived cyclic imino esters to nitroolefins
    Fang, Xin
    Dong, Xiu-Qin
    Wang, Chun-Jiang
    TETRAHEDRON LETTERS, 2014, 55 (41) : 5660 - 5662
  • [29] Organocatalytic Asymmetric Vinylogous Michael Reactions
    Yin, Yanli
    Jiang, Zhiyong
    CHEMCATCHEM, 2017, 9 (23) : 4306 - 4318
  • [30] Highly Enantioselective Organocatalytic Michael Addition of Ketones to Nitroolefins in the Presence of Water
    Chen, Qiankun
    Qiao, Yupu
    Ni, Bukuo
    SYNLETT, 2013, 24 (07) : 839 - 842